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Synthesis 1999; 1999(5): 745-747
DOI: 10.1055/s-1999-3460
short paper
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A Facile Synthesis of (S)-4-Hydroxypyrrolidin-2-one from (S)-Malic Acid

Masahiko Seki* , Kazuhiko Kondo
  • *Discovery Research Laboratory, Tanabe Seiyaku Co., Ltd., 3-16-89, Kashima, Yodogawa-ku, Osaka 532-8505, Japan; Fax +81(6)63 00 28 16; E-mail: k-kondo@tanabe.co.jp
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Publication Date:
31 December 1999 (online)

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The chiral diol methyl 3,4-dihydroxybutanoate 4b obtained from (S)-malic acid dimethyl ester (3b) was subjected to regioselective tosylation to give the tosylate 6 in good yield. Subsequent treatment of 6 with aqueous ammonia afforded (S)-4-hydroxypyrrolidin-2-one (1) through three steps in 32% overall yield from 3b.

tosylation - amination - reduction - regioselective reaction