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Note | Regular issue | Vol 53, No. 1, 2000, pp.173-181
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8689
Efficient Syntheses of (S)-4-Hydroxy-2-pyrrolidinone Derivatives

Osamu Kanno, Masao Miyauchi, and Isao Kawamoto*

*Medicinal Chemistry Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan

Abstract

Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone ((S)-2) and (R)-4-acetylthio-2-pyrrolidinone (5), which are key intermediates of oral carbapenem CS-834, were studied. The most efficient route to (S)-2 from (S)-3-hydroxybutyrolactone (8) was accomplished in high yield via (S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide (14).