Silane reduction of 5-hydroxy-6-methyl-pyridine-3,4-dicarboxylic acid diethyl ester: Synthesis of vitamin B6

Molecules

Volumn 8, Issue 12, 2003, Pages 873-881

  Dumond, Yves René ^a   Gum, Andrew G ^a  

^a DSM NUTRITIONAL PRODUCTS LTD   (Switzerland)

Author keywords

Ester reduction; Polymethylhydrosiloxane (PMHS); Pyridoxine; Silanes; Vitamin B6

Indexed keywords

5 HYDROXY 6 METHYLPYRIDINE 3,4 DICARBOXYLIC ACID DIETHYL ESTER; ESTER DERIVATIVE; PYRIDOXINE; SILANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; DRUG DESIGN; DRUG PURITY; DRUG SYNTHESIS; QUANTUM YIELD; REDUCTION; SEPARATION TECHNIQUE;

EID: 3342955367     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/81200873     Document Type: Article

References (58)

1. rd Edition; John Wiley & Sons, Inc.: New York, 1984; vol. 24, pp. 94-107.
2. 6" in Ullmann's Encyclopedia of Industrial Chemistry; VCH Verlagsgesellschaft mbH: Weinheim, Germany, 1996; vol. A27, pp. 530-540.
3. Kondrat'eva, G. Y. Khim. Nauk Prom. 1957, 2, 666.
4. Kondrat'eva, G. Y. Izv. Akad. Nauk SSSR, Ser. Khim. 1959, 484.
5. Kondrat'eva, G. Y. Dokl. Akad. Nauk SSSR 1961, 141, 628, 861 [Proc. Acad. Sci. USSR, Chem. Sect. 1961, 1169, 1221].
6. Kondrat'eva, G. Y. Dokl. Akad. Nauk SSSR 1961, 141, 628, 861 [Proc. Acad. Sci. USSR, Chem. Sect. 1961, 1169, 1221].
7. Huang C. H.; Kondrat'eva, G. Y. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1962, 525.
8. Harris, E. E.; Firestone, R. A.; Pfister, K.; Boettcher, R. R.; Cross, F. J.; Currie, R. B.; Monaco, M.; Peterson, E. R.; Reuter, W. J. Org. Chem. 1962, 27, 2705.
9. Firestone, R. A.; Harris, E. E.; Reuter, W. Tetrahedron 1967, 23, 943.
10. Pfister III, K.; Harris, E.; Firestone, R. A. Merck & Co., US 3,227,722, 4 Jan. 1966.
11. Naito, T.; Yoshikawa, T. Chem. Pharm. Bull. 1966, 14, 921.
12. Doktorova, N. D.; Ionova, L. V.; Karpeisky, M. Y.; Padyukova, N. S.; Turchin, K. F.; Florentiev, V. L. Tetrahedron, 1969, 25, 3527.
13. Itov Z. I.; Gunar, V. I. Chem. Pharm. J. (Engl. Transl.) 1988, 2, 151.
14. Kreher, R. Houben-Weyl Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart-New York, 1992; Band E7b Hetearene II Teil 2, Chap 4.2.1.3.4, pp. 532-539.
15. Karpeiskii, M. Y.; Florent'ev, V. L. Russ. Chem. Rev. 1969, 38, 540 and references therein.
16. Turchi, I. J.; Dewar, M. J. S. Chem. Rev. 1975, 75, 389 and references therein.
17. Boger, D. A. Chem. Rev. 1986, 86, 781.
18. Jones R. G.; Kornfeld, E.C. J. Am. Chem. Soc. 1951, 73, 107.
19. Lutz, A. H.; F. Hoffmann La Roche & Co., CH 408914, Switzerland, 1966.
20. Merck & Co., Inc., GB 1,116,118 [US 3,410,862], London, UK, 6 June 1968.
21. Jones, R. G. E. Lilly & Co., US 2,744,114, 1 May 1952.
22. Okawara, R.; Sakiyama, M. Bull. Chem. Soc. Jpn. 1956, 29, 236.
23. Koerner, G. Th. Goldschmidt A. G., DE 1,162,365, 5 May 1962.
24. Sagami Chemical Research Center, GB 1,401,948, 28 Feb. 1974.
25. Nagai, Y.; Ojima, I.; Inaba, S. Sagami Chemical Research Center, US 3,910,980, 7 Oct. 1975.
26. Kötzsch, H. J.; Seiler, C. D.; Vahlensieck, H. J. Dynamit Nobel A. G., US 4,228,092, 14 Oct. 1980.
27. Boyer, J.; Corriu, R. J. P.; Perz, R.; Reye, C. Tetrahedron 1981, 37, 2165.
28. Chuit, C.; Corriu, R. J. P.; Perz, R.; Reye, C. Synthesis 1981, 981.
29. Berk, S. C.; Buchwald, S. L. J. Org. Chem. 1992, 57, 3751.
30. Berk, S. C.; Buchwald, S. L. J. Org. Chem. 1993, 58, 3221.
31. Buchwald, S. L.; Gutierrez, A.; Berk, S. C.; Kreutzer, K. A. Massachusetts Institute of Technology, US 5,220,020, 15 Jun. 1993.
32. Breeden, S. W.; Lawrence, N. J. Synlett 1994, 833.
33. Mimoun, H. Firmenich, WO 96/12694, 2 May 1996.
34. Mimoun, H. Firmenich, WO 96/28497, 19 Sept. 1996.
35. Mimoun, H. Firmenich, WO 99/50211, 7 Oct. 1999.
36. Mimoun, H. J. Org. Chem. 1999, 64, 2582.
37. Mimoun, H.; de Saint Laumer, J. Y.; Giannini, L.; Scopelliti, R.; Floriani, C. J. Am. Chem. Soc. 1999, 121, 6158.
38. Kohra, S.; Hayashida, H.; Tominaga, Y.; Hosomi, A. Tetrahedron Lett. 1988, 29, 89.
39. Hosomi, A. Chisso Corporation, JP 63,010,738, 18 Jan. 1988.
40. Hojo, M.; Murakami, C.; Fuji, A.; Hosomi, A. Tetrahedron Lett. 1999, 40, 911.
41. Corriu, R. J. P.; Guerin, C.; Henner, B.; Wang, Q. Organometallics 1991, 10, 2297.
42. Corriu, R. J. P.; Guerin, C.; Henner, B.; Wang, Q, Inorg. Chim. Acta 1992, 198-200, 705.
43. Deneux, M.; Akhrem, I. C.; Avetissian, D. V.; Myssoff, E. I.; Volp'in, M. E. Bull. Soc. Chim. Fr. 1973, 2638.
44. Akhrem, I. S.; M. Dene, M.; Volp'in, M. E. Izv. Akad. Nauk SSSR Ser. Khim. (Engl. Transl.) 1973, 897.
45. Boyer, J.; Corriu, R. J. P.; Poirier, M.; Reye, C. Synthesis 1981, 558.
46. Boyer, J.; Corriu, R. J. P.; Perz, R.; Reye, C. Tetrahedron 1981, 17, 2165.
47. Chuit, C.; Corriu, R. J. P.; Perz, R.; Reye, C. Synthesis 1982, 981.
48. Fujit, M.; T. Hiyama, T. J. Org. Chem. 1988, 53, 5405.
49. Furin, G. G.; Vyazankina, O. A; Gostevsky, B. A.; Vyazankin, N. S. Tetrahedron 1988, 44, 2675.
50. Goldberg, Y.; Abele, E.; Shymanska, M.; Lukevics, E. J. Organomet. Chem. 1991, 410, 127.
51. Drew, M. D.; Lawrence, N. J.; Fontaine, D.; Sehkri, L. Synlett 1997, 989.
52. Drew, M. D.; Lawrence, N. J. Tetrahedron Lett. 1997, 38, 5857.
53. Kobayashi, Y.; Takahisa, E.; Nakano, M.; Watani, K. Tetrahedron 1997, 53, 1627.
54. Kobayashi, Y. Shin-Etsu Chemical Industry Co., JP 10,087,530, 7 Apr. 1998.
55. Lawrence, N. J.; Drew, M. D.; Bushell, S. M. J. Chem. Soc., Perkin Trans. 1 1999, 3381.
56. Abele, E.; Lukevics, E. Main Group Met. Chem. 2001, 24, 315.
57. Asakawa, H.; Fukushima, Y.; Imamiya, E.; Kawamatsu, Y. Chem. Pharm. Bull. 1979, 27, 522.
58. Goldberg, Y.; Abele, E.; Shymanska, M.; Lukevics, E. J. Organomet. Chem. 1991, 410, 127.