A practical, two-stage preparation of benzyl (3R)-3-amino-2-oxo-1-pyrrolidinecarboxylate (2S, 3S)-2, 3-bis [(4-methylbenzoyl) oxy] butanediote (2: 1)

…, KS Cardwell, JWB Cooke, RM Lawrence, P Scott…

Index: Barrett, Roger; Caine, Darren M.; Cardwell, Kevin S.; Cooke, Jason W.B.; Lawrence, Ron M.; Scott, Peter; Sjolin, Asa Tetrahedron Asymmetry, 2003 , vol. 14, # 22 p. 3627 - 3631

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Citation Number: 7

Abstract

Pyrrolidine-trans-lactams have emerged recently as attractive templates around which selective serine protease inhibitors can be developed. 1., 2. and 3. A recent example is the potent, human neutrophil elastase inhibitor 1, 4 which is of interest as a potential therapy for respiratory diseases such as cystic fibrosis and chronic bronchitis. A key intermediate in the preparation of these compounds is benzyl (3R)-3-amino-2-oxo-1-pyrrolidinecarboxylate (R)-2 (Scheme 1). 5 Herein we ...