A facile synthesis of (S)-4-hydroxypyrrolidin-2-one from (S)-malic acid

Synthesis

Volumn , Issue 5, 1999, Pages 745-747

  Seki, Masahiko ^a   Kondo, Kazuhiko ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

Amination; Reduction; Regioselective reaction; Tosylation

Indexed keywords

4 HYDROXYPYRROLIDIN 2 ONE; MALIC ACID; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHIRALITY; EPOXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032914264     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3460     Document Type: Article

References (19)

1. Matsumoto, T.; Trueb, W.; Gwinner, R.; Eugster, C. H. Helv. Chim. Acta 1969, 52, 716.
2. Banfi, S.; Fonio, W.; Allievi, E.; Pinza, M.; Dorigotti, L. Farmaco. Ed. Sci. 1984, 39, 16.
3. For example, see: Jung, M. E.; Shaw, T. J. J. Am. Chem. Soc. 1980, 102, 6304 and references cited therein.
4. Miyauchi, M.; Endo, R.; Hisaoka, M.; Yasuda, H.; Kawamoto, I. J. Antibiot. 1997, 50, 429. Iwasaki, T.; Kondo, K.; Horikawa, H.; Yamaguchi, T.; Matsushita, T. US Patent 5153187, Oct. 6, 1992.
5. Miyauchi, M.; Endo, R.; Hisaoka, M.; Yasuda, H.; Kawamoto, I. J. Antibiot. 1997, 50, 429. Iwasaki, T.; Kondo, K.; Horikawa, H.; Yamaguchi, T.; Matsushita, T. US Patent 5153187, Oct. 6, 1992.
6. Haeusler, J. Monatsh. Chem, 1987, 118, 865.
7. Srairi, D.; Maurey, G. Bull, Soc. Chim. Fr. 1987, 297.
8. Pellegata, R.; Dosi, I.; Villa, M.; Lesma, G.; Palmisano, G. Tetrahedron 1985, 41, 5607. Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1990, 376.
9. Pellegata, R.; Dosi, I.; Villa, M.; Lesma, G.; Palmisano, G. Tetrahedron 1985, 41, 5607. Orena, M.; Porzi, G.; Sandri, S. J. Chem. Res. (S) 1990, 376.
10. Santaniello, E.; Casati, R.; Milani, F. J. Chem. Res. (S) 1984, 132.
11. Zhou, B.; Gopalan, A. S.; VanMiddlesworth, F.; Shich, W-R.; Sih, C. J. Am. Chem. Soc. 1983, 105, 5925. Shimizu, S.; Kataoka, M.; Morishima, A.; Katoh, M.; Morikawa, T.; Miyoshi, T.; Yamada, H. Biotechnology Lett. 1990, 12, 593.
12. Zhou, B.; Gopalan, A. S.; VanMiddlesworth, F.; Shich, W-R.; Sih, C. J. Am. Chem. Soc. 1983, 105, 5925. Shimizu, S.; Kataoka, M.; Morishima, A.; Katoh, M.; Morikawa, T.; Miyoshi, T.; Yamada, H. Biotechnology Lett. 1990, 12, 593.
13. Kitamura, M.; Ohkuma, T.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1988, 29, 1555.
14. Suzuki, T.; Idogaki, H.; Kasai, N. Tetrahedron: Asymmetry 1996, 7, 3109.
15. 3 were necessary to consume all of the carboxylic acid 3a as described in the literature: Papageorgious, C.; Benezra, C. J. Org. Chem, 1985, 50, 1145.
16. (a) Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1389.
17. (b) Saito, S.; Ishikawa, T.; Kuroda, A.; Koga, K.; Moriwake, T. Tetrahedron 1992, 48, 4067.
18. Pellegata, R.; Pinza, M.; Pifferi, G. Synthesis 1978, 614.
19. 8