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New Technical Synthesis of Ethyl (R)-2-Hydroxy-4-phenylbutyrate of High Enantiomeric Purity

✍ Scribed by P Herold; A.F Indolese; M Studer; H.P Jalett; U Siegrist; H.U Blaser

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 81 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00617-7

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✦ Synopsis

AbstractÐA new technical synthesis to produce ethyl (R)-2-hydroxy-4-phenylbutyrate (5), an important intermediate for several ACE inhibitors with .99% ee in an over-all yield of 50±60% is described starting from acetophenone and diethyl oxalate. Key step is the chemoand enantioselective hydrogenation of ethyl 2,4-dioxo-4-phenylbutyrate (6) (ee up to 86%) catalyzed by a heterogeneous Pt catalyst modi®ed with dihydrocinchonidine, followed by crystallization of the 2-hydroxy-4-oxo ester 7 and hydrogenolysis of the 4-keto group.

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