Tetrahedron

Syntheses of (3S)-3-hydroxy-2-pyrrolidinone from (S)-malic acid

R Pires, K Burger

Index: Pires, Raul; Burger, Klaus Tetrahedron, 1997 , vol. 53, # 27 p. 9213 - 9218

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Citation Number: 16

Abstract

(S)-Malic acid 2 is transformed into (3S)-3-hydroxy-2-pyrrolidinone (8) using hexafluoro- acetone as protecting and activating agent. Two alternative routes were developed; key step of both routes is the intramolecular aminolytic cleavage of the lactone ring of the intermediate, 5-(2-aminoethyl)-2, 2-bis (trifluoromethyl)-1, 3-dioxolan-4-one (7).