A New Practical Synthesis of Ethyl (R)-(-)-4-Cyano-3-hydroxybutyrate From (S)-3-chloro-1,2-propanediol

Chengjun      Jiang; Huabin      Hong

doi:10.2174/157017812802139654

Abstract

A practical chemical synthesis of ethyl (R)-(-)-4-Cyano-3-hydroxybutyrate((R)-CNHB) has been accomplished from (S)-3-chloro-1,2-propanediol, which is a main by-product originating from (S,S)-Salen Co(III) catalyzed by hydrolytic kinetic resolution (HKR) of epichlorohydrin. The new synthetic approach demonstrated an efficient utilization of organic by-product for the asymmetric synthesis of the intermediate of atorvastatin.

Keywords: Atorvastatin, epichlorohydrin, by-product, (R)-(-)-4-Cyano-3-hydroxybutyrate, kinase, sterols, cholesterol, 2-propanediol, cyanide, thionyl

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Letters in Organic Chemistry

Title:A New Practical Synthesis of Ethyl (R)-(-)-4-Cyano-3-hydroxybutyrate From (S)-3-chloro-1,2-propanediol

Volume: 9 Issue: 7

Author(s): Chengjun Jiang and Huabin Hong

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Keywords: Atorvastatin, epichlorohydrin, by-product, (R)-(-)-4-Cyano-3-hydroxybutyrate, kinase, sterols, cholesterol, 2-propanediol, cyanide, thionyl

Abstract: A practical chemical synthesis of ethyl (R)-(-)-4-Cyano-3-hydroxybutyrate((R)-CNHB) has been accomplished from (S)-3-chloro-1,2-propanediol, which is a main by-product originating from (S,S)-Salen Co(III) catalyzed by hydrolytic kinetic resolution (HKR) of epichlorohydrin. The new synthetic approach demonstrated an efficient utilization of organic by-product for the asymmetric synthesis of the intermediate of atorvastatin.

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Jiang Chengjun and Hong Huabin, A New Practical Synthesis of Ethyl (R)-(-)-4-Cyano-3-hydroxybutyrate From (S)-3-chloro-1,2-propanediol, Letters in Organic Chemistry 2012; 9 (7) . https://dx.doi.org/10.2174/157017812802139654