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Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (12): 1997-1999. Previous Articles     Next Articles

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(R)-4-氰基-3-羟基丁酸乙酯的合成

吕世翔a；郭阳辉b；王亚平b；王相晶a；向文胜*,a   

  1. (a东北农业大学生物化工系 哈尔滨 150030) 
    (b浙江海正药业股份有限公司 台州 318000)
  • 收稿日期:2009-02-16 修回日期:2009-06-05 发布日期:2009-07-08
  • 通讯作者: 向文胜 E-mail:13857680603
  • 基金资助:

    国家支撑计划(No. 2006BAD31B02)；黑龙江省杰出青年基金(No. JC200706)资助项目

Synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester

Lü, Shixianga；Guo, Yanghuib；Wang, Yapingb；Wang, Xiangjinga；Xiang, Wensheng*,a   

  1. (a Department of Biochemical Engineering, Northeast Agricultural University, Harbin 150030) (b Zhejiang Hisun Pharmaceutical Co., Ltd, Taizhou 318000)
  • Received:2009-02-16 Revised:2009-06-05 Published:2009-07-08

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A novel method for synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester (1), a key intermediate of statins, was reported. The target compound 1 was successfully prepared via esterification, reduction, bromization and cyanation processes by using L-(—)-malic acid (2), which is an inexpensive and easily available starting material. The overall yield was 56.7%. The structures of intermediates and final product were determined by ESI-MS, 1H NMR, 13C NMR techniques, optical rotation and comparison with reported data. This method with the advantages of simply available starting material, easily conducted procedure, relatively high yield and easy purification is more suitable for scale-up production.

Key words: (R)-4-cyano-3-hydroxybutyric acid ethyl ester, L-(—)-malic acid, (3S)-3,4-dihydroxybutyric acid ethyl ester, (S)-4-bromo-3-hydroxybutyric acid ester, synthesis