Optical resolution of a 1,5-benzothiazepine derivative, a synthetic intermediate of diltiazem, by preferential crystallization and diastereomeric salt formation

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 12, 1997, Pages 1922-1927

  Yamada, Shin Ichi ^a   Yoshioka, Ryuzo ^a   Shibatani, Takeji ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

Diastereomeric salt; Diltiazem; Optical resolution; Preferential crystallization

Indexed keywords

5 [2 (DIMETHYL AMINO)ETHYL] 2,3 DIHYDRO 3 HYDROXY 2 (4 METHOXYPHENYL) 1,5 BENZOTHIAZEPIN 4(5H)ONE; BENZOTHIAZEPINE DERIVATIVE; DILTIAZEM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM ANTAGONISM; CRYSTALLIZATION; DRUG FORMULATION; DRUG MANUFACTURE; DRUG SYNTHESIS; OPTICAL RESOLUTION; PHYSICAL CHEMISTRY; REPRODUCIBILITY; STEREOISOMERISM;

EID: 0031471125     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.1922     Document Type: Article

References (40)

1. Abe K., Inoue H., Nagao T., Yakugaku Zasshi, 108, 716-732 (1988).
2. For examples of preferential crystallization procedure, see: a) Industria Chimica Profarmaco S.p.A. Jpn. Patent 2-1466 (1990) [Chem. Abstr., 112, 98206a (1990)]; b) Fabbrica Italiana Sintetici S.p.A. Can. Patent 2030375 (1991) [Chem. Abstr., 115, 280558f (1991)]; Zambon Group S.p.A. Jpn. Patent 3-188059 (1991) [Chem. Abstr., 115, 135687t (1991)].
3. For examples of preferential crystallization procedure, see: a) Industria Chimica Profarmaco S.p.A. Jpn. Patent 2-1466 (1990) [Chem. Abstr., 112, 98206a (1990)]; b) Fabbrica Italiana Sintetici S.p.A. Can. Patent 2030375 (1991) [Chem. Abstr., 115, 280558f (1991)]; Zambon Group S.p.A. Jpn. Patent 3-188059 (1991) [Chem. Abstr., 115, 135687t (1991)].
4. For examples of preferential crystallization procedure, see: a) Industria Chimica Profarmaco S.p.A. Jpn. Patent 2-1466 (1990) [Chem. Abstr., 112, 98206a (1990)]; b) Fabbrica Italiana Sintetici S.p.A. Can. Patent 2030375 (1991) [Chem. Abstr., 115, 280558f (1991)]; Zambon Group S.p.A. Jpn. Patent 3-188059 (1991) [Chem. Abstr., 115, 135687t (1991)].
5. For examples of diastereomeric salt procedure, see: a) Inoue H., Takeo S., Kawazu M., Kugita H., Yakugaku Zasshi, 93, 729-732 (1973); b) Istituto Luso Farmaco D'Italia S.p.A. U.S. Patent 4533748 (1983) [Chem. Abstr., 101, 110549x (1984)]; Kojić-Prodić B., Ružić-Toroš Ž., Šunjić V., Decorte E., Moimas F., Helv. Chim. Acta, 67, 916-926 (1984); Senuma M., Shibazaki M., Nishimoto S., Shibata K., Okamura K., Date T., Chem. Pharm. Bull., 37, 3204-3208 (1989); e) Zambon Group S.p.A. U.S. Patent 5144025 (1990) [Chem. Abstr., 114, 122436q (1991)]; f) Yamamoto M., Hayashi M., Masaki M., Nohira, H., Tetrahedron: Asymmetry, 2, 403-406 (1991); g) Gizur T., Harsányi K., Fogassy E., J. Prakt. Chem., 336, 628-631 (1994) and references cited therein.
6. For examples of diastereomeric salt procedure, see: a) Inoue H., Takeo S., Kawazu M., Kugita H., Yakugaku Zasshi, 93, 729-732 (1973); b) Istituto Luso Farmaco D'Italia S.p.A. U.S. Patent 4533748 (1983) [Chem. Abstr., 101, 110549x (1984)]; Kojić-Prodić B., Ružić-Toroš Ž., Šunjić V., Decorte E., Moimas F., Helv. Chim. Acta, 67, 916-926 (1984); Senuma M., Shibazaki M., Nishimoto S., Shibata K., Okamura K., Date T., Chem. Pharm. Bull., 37, 3204-3208 (1989); e) Zambon Group S.p.A. U.S. Patent 5144025 (1990) [Chem. Abstr., 114, 122436q (1991)]; f) Yamamoto M., Hayashi M., Masaki M., Nohira, H., Tetrahedron: Asymmetry, 2, 403-406 (1991); g) Gizur T., Harsányi K., Fogassy E., J. Prakt. Chem., 336, 628-631 (1994) and references cited therein.
7. For examples of diastereomeric salt procedure, see: a) Inoue H., Takeo S., Kawazu M., Kugita H., Yakugaku Zasshi, 93, 729-732 (1973); b) Istituto Luso Farmaco D'Italia S.p.A. U.S. Patent 4533748 (1983) [Chem. Abstr., 101, 110549x (1984)]; Kojić-Prodić B., Ružić-Toroš Ž., Šunjić V., Decorte E., Moimas F., Helv. Chim. Acta, 67, 916-926 (1984); Senuma M., Shibazaki M., Nishimoto S., Shibata K., Okamura K., Date T., Chem. Pharm. Bull., 37, 3204-3208 (1989); e) Zambon Group S.p.A. U.S. Patent 5144025 (1990) [Chem. Abstr., 114, 122436q (1991)]; f) Yamamoto M., Hayashi M., Masaki M., Nohira, H., Tetrahedron: Asymmetry, 2, 403-406 (1991); g) Gizur T., Harsányi K., Fogassy E., J. Prakt. Chem., 336, 628-631 (1994) and references cited therein.
8. For examples of diastereomeric salt procedure, see: a) Inoue H., Takeo S., Kawazu M., Kugita H., Yakugaku Zasshi, 93, 729-732 (1973); b) Istituto Luso Farmaco D'Italia S.p.A. U.S. Patent 4533748 (1983) [Chem. Abstr., 101, 110549x (1984)]; Kojić-Prodić B., Ružić-Toroš Ž., Šunjić V., Decorte E., Moimas F., Helv. Chim. Acta, 67, 916-926 (1984); Senuma M., Shibazaki M., Nishimoto S., Shibata K., Okamura K., Date T., Chem. Pharm. Bull., 37, 3204-3208 (1989); e) Zambon Group S.p.A. U.S. Patent 5144025 (1990) [Chem. Abstr., 114, 122436q (1991)]; f) Yamamoto M., Hayashi M., Masaki M., Nohira, H., Tetrahedron: Asymmetry, 2, 403-406 (1991); g) Gizur T., Harsányi K., Fogassy E., J. Prakt. Chem., 336, 628-631 (1994) and references cited therein.
9. For examples of diastereomeric salt procedure, see: a) Inoue H., Takeo S., Kawazu M., Kugita H., Yakugaku Zasshi, 93, 729-732 (1973); b) Istituto Luso Farmaco D'Italia S.p.A. U.S. Patent 4533748 (1983) [Chem. Abstr., 101, 110549x (1984)]; Kojić-Prodić B., Ružić-Toroš Ž., Šunjić V., Decorte E., Moimas F., Helv. Chim. Acta, 67, 916-926 (1984); Senuma M., Shibazaki M., Nishimoto S., Shibata K., Okamura K., Date T., Chem. Pharm. Bull., 37, 3204-3208 (1989); e) Zambon Group S.p.A. U.S. Patent 5144025 (1990) [Chem. Abstr., 114, 122436q (1991)]; f) Yamamoto M., Hayashi M., Masaki M., Nohira, H., Tetrahedron: Asymmetry, 2, 403-406 (1991); g) Gizur T., Harsányi K., Fogassy E., J. Prakt. Chem., 336, 628-631 (1994) and references cited therein.
10. For examples of diastereomeric salt procedure, see: a) Inoue H., Takeo S., Kawazu M., Kugita H., Yakugaku Zasshi, 93, 729-732 (1973); b) Istituto Luso Farmaco D'Italia S.p.A. U.S. Patent 4533748 (1983) [Chem. Abstr., 101, 110549x (1984)]; Kojić-Prodić B., Ružić-Toroš Ž., Šunjić V., Decorte E., Moimas F., Helv. Chim. Acta, 67, 916-926 (1984); Senuma M., Shibazaki M., Nishimoto S., Shibata K., Okamura K., Date T., Chem. Pharm. Bull., 37, 3204-3208 (1989); e) Zambon Group S.p.A. U.S. Patent 5144025 (1990) [Chem. Abstr., 114, 122436q (1991)]; f) Yamamoto M., Hayashi M., Masaki M., Nohira, H., Tetrahedron: Asymmetry, 2, 403-406 (1991); g) Gizur T., Harsányi K., Fogassy E., J. Prakt. Chem., 336, 628-631 (1994) and references cited therein.
11. For examples of diastereomeric salt procedure, see: a) Inoue H., Takeo S., Kawazu M., Kugita H., Yakugaku Zasshi, 93, 729-732 (1973); b) Istituto Luso Farmaco D'Italia S.p.A. U.S. Patent 4533748 (1983) [Chem. Abstr., 101, 110549x (1984)]; Kojić-Prodić B., Ružić-Toroš Ž., Šunjić V., Decorte E., Moimas F., Helv. Chim. Acta, 67, 916-926 (1984); Senuma M., Shibazaki M., Nishimoto S., Shibata K., Okamura K., Date T., Chem. Pharm. Bull., 37, 3204-3208 (1989); e) Zambon Group S.p.A. U.S. Patent 5144025 (1990) [Chem. Abstr., 114, 122436q (1991)]; f) Yamamoto M., Hayashi M., Masaki M., Nohira, H., Tetrahedron: Asymmetry, 2, 403-406 (1991); g) Gizur T., Harsányi K., Fogassy E., J. Prakt. Chem., 336, 628-631 (1994) and references cited therein.
12. For examples of biochemical procedure, see: a) Gentile A., Giordano C., Fuganti C., Ghirotto L., Servi S., J. Org. Chem., 57, 6635-6637 (1992); b) Inoue H., Matsuki K., Oh-ishi T., Chem. Pharm. Bull., 41, 1521-1523 (1993); Nishida T., Matsumae H., Machida I., Shibatani T., Biocatalysis and Biotransformation, 12, 205-214 (1995); Akita H., Umezawa I., Matsukura H., Oishi T., Chem. Pharm. Bull., 40, 318-324 (1992); e) Matsumae H., Furui M., Shibatani T., J. Ferment. Bioeng., 75, 93-98 (1993); f) Kanerva L. T., Sundholm O., J. Chem. Soc., Perkin Trans. 1, 1993, 1385-1389; g) Idem, ibid., 1993, 2407-2410; h) Desai S. B., Argade N. P., Ganesh K. N., J. Org. Chem., 61, 6730-6732 (1996); Akita H., Umezawa I., Matsukura H., Chem. Pharm. Bull., 45, 272-278 (1997); j) Tanabe Seiyaku Co., Ltd. Jpn. Patent 9-9991 (1997) [Chem. Abstr., 126, 185076r (1997)].
13. For examples of biochemical procedure, see: a) Gentile A., Giordano C., Fuganti C., Ghirotto L., Servi S., J. Org. Chem., 57, 6635-6637 (1992); b) Inoue H., Matsuki K., Oh-ishi T., Chem. Pharm. Bull., 41, 1521-1523 (1993); Nishida T., Matsumae H., Machida I., Shibatani T., Biocatalysis and Biotransformation, 12, 205-214 (1995); Akita H., Umezawa I., Matsukura H., Oishi T., Chem. Pharm. Bull., 40, 318-324 (1992); e) Matsumae H., Furui M., Shibatani T., J. Ferment. Bioeng., 75, 93-98 (1993); f) Kanerva L. T., Sundholm O., J. Chem. Soc., Perkin Trans. 1, 1993, 1385-1389; g) Idem, ibid., 1993, 2407-2410; h) Desai S. B., Argade N. P., Ganesh K. N., J. Org. Chem., 61, 6730-6732 (1996); Akita H., Umezawa I., Matsukura H., Chem. Pharm. Bull., 45, 272-278 (1997); j) Tanabe Seiyaku Co., Ltd. Jpn. Patent 9-9991 (1997) [Chem. Abstr., 126, 185076r (1997)].
14. For examples of biochemical procedure, see: a) Gentile A., Giordano C., Fuganti C., Ghirotto L., Servi S., J. Org. Chem., 57, 6635-6637 (1992); b) Inoue H., Matsuki K., Oh-ishi T., Chem. Pharm. Bull., 41, 1521-1523 (1993); Nishida T., Matsumae H., Machida I., Shibatani T., Biocatalysis and Biotransformation, 12, 205-214 (1995); Akita H., Umezawa I., Matsukura H., Oishi T., Chem. Pharm. Bull., 40, 318-324 (1992); e) Matsumae H., Furui M., Shibatani T., J. Ferment. Bioeng., 75, 93-98 (1993); f) Kanerva L. T., Sundholm O., J. Chem. Soc., Perkin Trans. 1, 1993, 1385-1389; g) Idem, ibid., 1993, 2407-2410; h) Desai S. B., Argade N. P., Ganesh K. N., J. Org. Chem., 61, 6730-6732 (1996); Akita H., Umezawa I., Matsukura H., Chem. Pharm. Bull., 45, 272-278 (1997); j) Tanabe Seiyaku Co., Ltd. Jpn. Patent 9-9991 (1997) [Chem. Abstr., 126, 185076r (1997)].
15. For examples of biochemical procedure, see: a) Gentile A., Giordano C., Fuganti C., Ghirotto L., Servi S., J. Org. Chem., 57, 6635-6637 (1992); b) Inoue H., Matsuki K., Oh-ishi T., Chem. Pharm. Bull., 41, 1521-1523 (1993); Nishida T., Matsumae H., Machida I., Shibatani T., Biocatalysis and Biotransformation, 12, 205-214 (1995); Akita H., Umezawa I., Matsukura H., Oishi T., Chem. Pharm. Bull., 40, 318-324 (1992); e) Matsumae H., Furui M., Shibatani T., J. Ferment. Bioeng., 75, 93-98 (1993); f) Kanerva L. T., Sundholm O., J. Chem. Soc., Perkin Trans. 1, 1993, 1385-1389; g) Idem, ibid., 1993, 2407-2410; h) Desai S. B., Argade N. P., Ganesh K. N., J. Org. Chem., 61, 6730-6732 (1996); Akita H., Umezawa I., Matsukura H., Chem. Pharm. Bull., 45, 272-278 (1997); j) Tanabe Seiyaku Co., Ltd. Jpn. Patent 9-9991 (1997) [Chem. Abstr., 126, 185076r (1997)].
16. For examples of biochemical procedure, see: a) Gentile A., Giordano C., Fuganti C., Ghirotto L., Servi S., J. Org. Chem., 57, 6635-6637 (1992); b) Inoue H., Matsuki K., Oh-ishi T., Chem. Pharm. Bull., 41, 1521-1523 (1993); Nishida T., Matsumae H., Machida I., Shibatani T., Biocatalysis and Biotransformation, 12, 205-214 (1995); Akita H., Umezawa I., Matsukura H., Oishi T., Chem. Pharm. Bull., 40, 318-324 (1992); e) Matsumae H., Furui M., Shibatani T., J. Ferment. Bioeng., 75, 93-98 (1993); f) Kanerva L. T., Sundholm O., J. Chem. Soc., Perkin Trans. 1, 1993, 1385-1389; g) Idem, ibid., 1993, 2407-2410; h) Desai S. B., Argade N. P., Ganesh K. N., J. Org. Chem., 61, 6730-6732 (1996); Akita H., Umezawa I., Matsukura H., Chem. Pharm. Bull., 45, 272-278 (1997); j) Tanabe Seiyaku Co., Ltd. Jpn. Patent 9-9991 (1997) [Chem. Abstr., 126, 185076r (1997)].
17. For examples of biochemical procedure, see: a) Gentile A., Giordano C., Fuganti C., Ghirotto L., Servi S., J. Org. Chem., 57, 6635-6637 (1992); b) Inoue H., Matsuki K., Oh-ishi T., Chem. Pharm. Bull., 41, 1521-1523 (1993); Nishida T., Matsumae H., Machida I., Shibatani T., Biocatalysis and Biotransformation, 12, 205-214 (1995); Akita H., Umezawa I., Matsukura H., Oishi T., Chem. Pharm. Bull., 40, 318-324 (1992); e) Matsumae H., Furui M., Shibatani T., J. Ferment. Bioeng., 75, 93-98 (1993); f) Kanerva L. T., Sundholm O., J. Chem. Soc., Perkin Trans. 1, 1993, 1385-1389; g) Idem, ibid., 1993, 2407-2410; h) Desai S. B., Argade N. P., Ganesh K. N., J. Org. Chem., 61, 6730-6732 (1996); Akita H., Umezawa I., Matsukura H., Chem. Pharm. Bull., 45, 272-278 (1997); j) Tanabe Seiyaku Co., Ltd. Jpn. Patent 9-9991 (1997) [Chem. Abstr., 126, 185076r (1997)].
18. For examples of biochemical procedure, see: a) Gentile A., Giordano C., Fuganti C., Ghirotto L., Servi S., J. Org. Chem., 57, 6635-6637 (1992); b) Inoue H., Matsuki K., Oh-ishi T., Chem. Pharm. Bull., 41, 1521-1523 (1993); Nishida T., Matsumae H., Machida I., Shibatani T., Biocatalysis and Biotransformation, 12, 205-214 (1995); Akita H., Umezawa I., Matsukura H., Oishi T., Chem. Pharm. Bull., 40, 318-324 (1992); e) Matsumae H., Furui M., Shibatani T., J. Ferment. Bioeng., 75, 93-98 (1993); f) Kanerva L. T., Sundholm O., J. Chem. Soc., Perkin Trans. 1, 1993, 1385-1389; g) Idem, ibid., 1993, 2407-2410; h) Desai S. B., Argade N. P., Ganesh K. N., J. Org. Chem., 61, 6730-6732 (1996); Akita H., Umezawa I., Matsukura H., Chem. Pharm. Bull., 45, 272-278 (1997); j) Tanabe Seiyaku Co., Ltd. Jpn. Patent 9-9991 (1997) [Chem. Abstr., 126, 185076r (1997)].
19. For examples of biochemical procedure, see: a) Gentile A., Giordano C., Fuganti C., Ghirotto L., Servi S., J. Org. Chem., 57, 6635-6637 (1992); b) Inoue H., Matsuki K., Oh-ishi T., Chem. Pharm. Bull., 41, 1521-1523 (1993); Nishida T., Matsumae H., Machida I., Shibatani T., Biocatalysis and Biotransformation, 12, 205-214 (1995); Akita H., Umezawa I., Matsukura H., Oishi T., Chem. Pharm. Bull., 40, 318-324 (1992); e) Matsumae H., Furui M., Shibatani T., J. Ferment. Bioeng., 75, 93-98 (1993); f) Kanerva L. T., Sundholm O., J. Chem. Soc., Perkin Trans. 1, 1993, 1385-1389; g) Idem, ibid., 1993, 2407-2410; h) Desai S. B., Argade N. P., Ganesh K. N., J. Org. Chem., 61, 6730-6732 (1996); Akita H., Umezawa I., Matsukura H., Chem. Pharm. Bull., 45, 272-278 (1997); j) Tanabe Seiyaku Co., Ltd. Jpn. Patent 9-9991 (1997) [Chem. Abstr., 126, 185076r (1997)].
20. For examples of biochemical procedure, see: a) Gentile A., Giordano C., Fuganti C., Ghirotto L., Servi S., J. Org. Chem., 57, 6635-6637 (1992); b) Inoue H., Matsuki K., Oh-ishi T., Chem. Pharm. Bull., 41, 1521-1523 (1993); Nishida T., Matsumae H., Machida I., Shibatani T., Biocatalysis and Biotransformation, 12, 205-214 (1995); Akita H., Umezawa I., Matsukura H., Oishi T., Chem. Pharm. Bull., 40, 318-324 (1992); e) Matsumae H., Furui M., Shibatani T., J. Ferment. Bioeng., 75, 93-98 (1993); f) Kanerva L. T., Sundholm O., J. Chem. Soc., Perkin Trans. 1, 1993, 1385-1389; g) Idem, ibid., 1993, 2407-2410; h) Desai S. B., Argade N. P., Ganesh K. N., J. Org. Chem., 61, 6730-6732 (1996); Akita H., Umezawa I., Matsukura H., Chem. Pharm. Bull., 45, 272-278 (1997); j) Tanabe Seiyaku Co., Ltd. Jpn. Patent 9-9991 (1997) [Chem. Abstr., 126, 185076r (1997)].
21. For examples of biochemical procedure, see: a) Gentile A., Giordano C., Fuganti C., Ghirotto L., Servi S., J. Org. Chem., 57, 6635-6637 (1992); b) Inoue H., Matsuki K., Oh-ishi T., Chem. Pharm. Bull., 41, 1521-1523 (1993); Nishida T., Matsumae H., Machida I., Shibatani T., Biocatalysis and Biotransformation, 12, 205-214 (1995); Akita H., Umezawa I., Matsukura H., Oishi T., Chem. Pharm. Bull., 40, 318-324 (1992); e) Matsumae H., Furui M., Shibatani T., J. Ferment. Bioeng., 75, 93-98 (1993); f) Kanerva L. T., Sundholm O., J. Chem. Soc., Perkin Trans. 1, 1993, 1385-1389; g) Idem, ibid., 1993, 2407-2410; h) Desai S. B., Argade N. P., Ganesh K. N., J. Org. Chem., 61, 6730-6732 (1996); Akita H., Umezawa I., Matsukura H., Chem. Pharm. Bull., 45, 272-278 (1997); j) Tanabe Seiyaku Co., Ltd. Jpn. Patent 9-9991 (1997) [Chem. Abstr., 126, 185076r (1997)].
22. For examples of asymmetric syntheses, see: a) Fuji Chemical, Jpn. Patent 61-268663 (1986) [Chem. Abstr., 108, 131290r (1988)]; b) Marion Laboratories, Inc. Jpn. Patent 2-17169 (1990) [Chem. Abstr., 112, 198431p (1990)]; Schwartz A., Madan P. B., Mohacsi E., O'Brien J. P., Todaro L. J., Coffen D. L., J. Org. Chem., 57, 851-856 (1992); Matsuki K., Sobukawa M., Kawai A., Inoue H., Takeda M., Chem. Pharm. Bull., 41, 643-648 (1993); e) Genêt J. P., Andrade M. C. C., Ratovelomanana-Vidal V., Tetrahedron Lett., 36, 2063-2066 (1995); f) Takahashi T., Muraoka M., Capo M., Koga K., Chem. Pharm. Bull., 43, 1821-1823 (1995); g) Yamada S., Mori Y., Morimatsu K., Ishizu Y., Ozaki Y., Yoshioka R., Nakatani T., Seko H., J. Org. Chem., 61, 8586-8590 (1996) and references cited therein.
23. For examples of asymmetric syntheses, see: a) Fuji Chemical, Jpn. Patent 61-268663 (1986) [Chem. Abstr., 108, 131290r (1988)]; b) Marion Laboratories, Inc. Jpn. Patent 2-17169 (1990) [Chem. Abstr., 112, 198431p (1990)]; Schwartz A., Madan P. B., Mohacsi E., O'Brien J. P., Todaro L. J., Coffen D. L., J. Org. Chem., 57, 851-856 (1992); Matsuki K., Sobukawa M., Kawai A., Inoue H., Takeda M., Chem. Pharm. Bull., 41, 643-648 (1993); e) Genêt J. P., Andrade M. C. C., Ratovelomanana-Vidal V., Tetrahedron Lett., 36, 2063-2066 (1995); f) Takahashi T., Muraoka M., Capo M., Koga K., Chem. Pharm. Bull., 43, 1821-1823 (1995); g) Yamada S., Mori Y., Morimatsu K., Ishizu Y., Ozaki Y., Yoshioka R., Nakatani T., Seko H., J. Org. Chem., 61, 8586-8590 (1996) and references cited therein.
24. For examples of asymmetric syntheses, see: a) Fuji Chemical, Jpn. Patent 61-268663 (1986) [Chem. Abstr., 108, 131290r (1988)]; b) Marion Laboratories, Inc. Jpn. Patent 2-17169 (1990) [Chem. Abstr., 112, 198431p (1990)]; Schwartz A., Madan P. B., Mohacsi E., O'Brien J. P., Todaro L. J., Coffen D. L., J. Org. Chem., 57, 851-856 (1992); Matsuki K., Sobukawa M., Kawai A., Inoue H., Takeda M., Chem. Pharm. Bull., 41, 643-648 (1993); e) Genêt J. P., Andrade M. C. C., Ratovelomanana-Vidal V., Tetrahedron Lett., 36, 2063-2066 (1995); f) Takahashi T., Muraoka M., Capo M., Koga K., Chem. Pharm. Bull., 43, 1821-1823 (1995); g) Yamada S., Mori Y., Morimatsu K., Ishizu Y., Ozaki Y., Yoshioka R., Nakatani T., Seko H., J. Org. Chem., 61, 8586-8590 (1996) and references cited therein.
25. For examples of asymmetric syntheses, see: a) Fuji Chemical, Jpn. Patent 61-268663 (1986) [Chem. Abstr., 108, 131290r (1988)]; b) Marion Laboratories, Inc. Jpn. Patent 2-17169 (1990) [Chem. Abstr., 112, 198431p (1990)]; Schwartz A., Madan P. B., Mohacsi E., O'Brien J. P., Todaro L. J., Coffen D. L., J. Org. Chem., 57, 851-856 (1992); Matsuki K., Sobukawa M., Kawai A., Inoue H., Takeda M., Chem. Pharm. Bull., 41, 643-648 (1993); e) Genêt J. P., Andrade M. C. C., Ratovelomanana-Vidal V., Tetrahedron Lett., 36, 2063-2066 (1995); f) Takahashi T., Muraoka M., Capo M., Koga K., Chem. Pharm. Bull., 43, 1821-1823 (1995); g) Yamada S., Mori Y., Morimatsu K., Ishizu Y., Ozaki Y., Yoshioka R., Nakatani T., Seko H., J. Org. Chem., 61, 8586-8590 (1996) and references cited therein.
26. For examples of asymmetric syntheses, see: a) Fuji Chemical, Jpn. Patent 61-268663 (1986) [Chem. Abstr., 108, 131290r (1988)]; b) Marion Laboratories, Inc. Jpn. Patent 2-17169 (1990) [Chem. Abstr., 112, 198431p (1990)]; Schwartz A., Madan P. B., Mohacsi E., O'Brien J. P., Todaro L. J., Coffen D. L., J. Org. Chem., 57, 851-856 (1992); Matsuki K., Sobukawa M., Kawai A., Inoue H., Takeda M., Chem. Pharm. Bull., 41, 643-648 (1993); e) Genêt J. P., Andrade M. C. C., Ratovelomanana-Vidal V., Tetrahedron Lett., 36, 2063-2066 (1995); f) Takahashi T., Muraoka M., Capo M., Koga K., Chem. Pharm. Bull., 43, 1821-1823 (1995); g) Yamada S., Mori Y., Morimatsu K., Ishizu Y., Ozaki Y., Yoshioka R., Nakatani T., Seko H., J. Org. Chem., 61, 8586-8590 (1996) and references cited therein.
27. For examples of asymmetric syntheses, see: a) Fuji Chemical, Jpn. Patent 61-268663 (1986) [Chem. Abstr., 108, 131290r (1988)]; b) Marion Laboratories, Inc. Jpn. Patent 2-17169 (1990) [Chem. Abstr., 112, 198431p (1990)]; Schwartz A., Madan P. B., Mohacsi E., O'Brien J. P., Todaro L. J., Coffen D. L., J. Org. Chem., 57, 851-856 (1992); Matsuki K., Sobukawa M., Kawai A., Inoue H., Takeda M., Chem. Pharm. Bull., 41, 643-648 (1993); e) Genêt J. P., Andrade M. C. C., Ratovelomanana-Vidal V., Tetrahedron Lett., 36, 2063-2066 (1995); f) Takahashi T., Muraoka M., Capo M., Koga K., Chem. Pharm. Bull., 43, 1821-1823 (1995); g) Yamada S., Mori Y., Morimatsu K., Ishizu Y., Ozaki Y., Yoshioka R., Nakatani T., Seko H., J. Org. Chem., 61, 8586-8590 (1996) and references cited therein.
28. For examples of asymmetric syntheses, see: a) Fuji Chemical, Jpn. Patent 61-268663 (1986) [Chem. Abstr., 108, 131290r (1988)]; b) Marion Laboratories, Inc. Jpn. Patent 2-17169 (1990) [Chem. Abstr., 112, 198431p (1990)]; Schwartz A., Madan P. B., Mohacsi E., O'Brien J. P., Todaro L. J., Coffen D. L., J. Org. Chem., 57, 851-856 (1992); Matsuki K., Sobukawa M., Kawai A., Inoue H., Takeda M., Chem. Pharm. Bull., 41, 643-648 (1993); e) Genêt J. P., Andrade M. C. C., Ratovelomanana-Vidal V., Tetrahedron Lett., 36, 2063-2066 (1995); f) Takahashi T., Muraoka M., Capo M., Koga K., Chem. Pharm. Bull., 43, 1821-1823 (1995); g) Yamada S., Mori Y., Morimatsu K., Ishizu Y., Ozaki Y., Yoshioka R., Nakatani T., Seko H., J. Org. Chem., 61, 8586-8590 (1996) and references cited therein.
29. Synthelabo U.S. Patent 5013835 (1991) [Chem. Abstr., 114, 81901s (1991)].
30. Kugita H., Inoue H., Ikezaki M., Konda M., Takeo S., Chem. Pharm. Bull., 19, 595-602 (1971).
31. Jacques J., Collet A., Wilen S. H., "Enantiomers, Racemates, and Resolutions," John Wiley & Sons, Inc., 1981.
32. Asai S., Ind. Eng. Chem. Process Des. Dev., 22, 429-432 (1983).
33. Nohira H., Watanabe K., Kurokawa M., Chem. Lett., 1976, 299-300.
34. Allinger N. L., Eliel E. L., "Topics in Stereochemistry," Vol. 6, John Wiley & Sons, Inc., 1971, p. 139.
35. See for example: a) Fogassy E., Ács M., Faigl F., Simon K., Rohonczy J., Ecsery Z., J. Chem. Soc., Perkin Trans. 2, 1986, 1881-1886; b) van der Haest A. D., Wynberg H., Leusen F. J. J., Bruggink A., Recl. Trav. Chim. Pays-Bas, 109, 523-528 (1990); Yoshioka R., Ohtsuki O., Da-te T., Okamura K., Senuma M., Bull. Chem. Soc. Jpn., 67, 3012-3020 (1994); Kinbara K., Sakai K., Hashimoto Y., Nohira H., Saigo K., J. Chem. Soc., Perkin Trans. 2, 1996, 2615-2622.
36. See for example: a) Fogassy E., Ács M., Faigl F., Simon K., Rohonczy J., Ecsery Z., J. Chem. Soc., Perkin Trans. 2, 1986, 1881-1886; b) van der Haest A. D., Wynberg H., Leusen F. J. J., Bruggink A., Recl. Trav. Chim. Pays-Bas, 109, 523-528 (1990); Yoshioka R., Ohtsuki O., Da-te T., Okamura K., Senuma M., Bull. Chem. Soc. Jpn., 67, 3012-3020 (1994); Kinbara K., Sakai K., Hashimoto Y., Nohira H., Saigo K., J. Chem. Soc., Perkin Trans. 2, 1996, 2615-2622.
37. See for example: a) Fogassy E., Ács M., Faigl F., Simon K., Rohonczy J., Ecsery Z., J. Chem. Soc., Perkin Trans. 2, 1986, 1881-1886; b) van der Haest A. D., Wynberg H., Leusen F. J. J., Bruggink A., Recl. Trav. Chim. Pays-Bas, 109, 523-528 (1990); Yoshioka R., Ohtsuki O., Da-te T., Okamura K., Senuma M., Bull. Chem. Soc. Jpn., 67, 3012-3020 (1994); Kinbara K., Sakai K., Hashimoto Y., Nohira H., Saigo K., J. Chem. Soc., Perkin Trans. 2, 1996, 2615-2622.
38. See for example: a) Fogassy E., Ács M., Faigl F., Simon K., Rohonczy J., Ecsery Z., J. Chem. Soc., Perkin Trans. 2, 1986, 1881-1886; b) van der Haest A. D., Wynberg H., Leusen F. J. J., Bruggink A., Recl. Trav. Chim. Pays-Bas, 109, 523-528 (1990); Yoshioka R., Ohtsuki O., Da-te T., Okamura K., Senuma M., Bull. Chem. Soc. Jpn., 67, 3012-3020 (1994); Kinbara K., Sakai K., Hashimoto Y., Nohira H., Saigo K., J. Chem. Soc., Perkin Trans. 2, 1996, 2615-2622.
39. Kozma D., Nyéki Á., Ács M., Fogassy E., Tetrahedron: Asymmetry, 5, 315-316 (1994).
40. Seed crystals of (-)-7·AHS were prepared through conventional resolution (see refs. 3, 4).