Nitrilase-Catalysed Desymmetrisation of 3-Hydroxyglutaronitrile: Preparation of a Statin Side-Chain Intermediate

Bergeron, Sophie; A. Chaplin, David; H. Edwards, J.; S. W. Ellis, Brian; Hill, Catherine; E. Holt-Tiffin, Karen; R. Knight, Jonathan; Mahoney, Thomas; P. Osborne, Andrew; Ruecroft, Graham

doi:10.1021/op050257n

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Nitrilase-Catalysed Desymmetrisation of 3-Hydroxyglutaronitrile: Preparation of a Statin Side-Chain Intermediate

Published in Organic Process Research & Development • Apr 1, 2006

Authors:

Sophie Bergeron

David A. Chaplin

J. H. Edwards

Abstract

An efficient, scaleable synthesis of ethyl ( R )-4-cyano-3-hydroxybutyrate, a potential intermediate in the synthesis of Atorvastatin (Lipitor), has been developed. The three-stage process starts with reaction of low-cost epichlorohydrin with cyanide to give 3-hydroxyglutaronitrile (3-HGN). The seco...

Subject

Nitrilase

Chemistry

Substrate (aquarium)

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