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有机化学 ›› 2006, Vol. 26 ›› Issue (07): 950-953. 上一篇    下一篇

研究论文

盐酸L-肉碱和盐酸乙酰L-肉碱的合成

程青芳*,1,2，许兴友1,2，李艳辉1，王建1，姚泳3   

  1. (1淮海工学院化工系 连云港 222005)
    (2南京理工大学材料化学实验室 南京 210094)
    (3江苏正大天晴药业股份有限公司 连云港 222006)
  • 收稿日期:2005-05-12 修回日期:2005-10-17 发布日期:2006-07-01
  • 通讯作者: 程青芳

Enantioselective Synthesis of L-Carnitine and Ace-tyl-L-carnitine Hydrochlorides

CHENG Qing-Fang*,1,2,XU Xing-You1,2,LI Yan-Hui1,WANG Jian1,YAO Yong3   

  1. (1 Department of Chemical Technology, Huaihai Institute of Technology, Lianyungang 222005)
    (2 Materials Chemistry Laboratory, Nanjing University of Science and Technol-ogy, Nanjing 210094)
    (3 Jiangsu Zhengda Tianqing Pharmaceutical Co. Ltd., Lianyungang 222006)
  • Received:2005-05-12 Revised:2005-10-17 Published:2006-07-01
  • Contact: CHENG Qing-Fang

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L-肉碱(维生素BT)和乙酰L-肉碱是长链脂肪酸运输的载体, 广泛用于医药、保健食品及饲料等行业. 本工作介绍了一种化学不对称合成盐酸L-肉碱和盐酸乙酰L-肉碱的方法. 以自制的手性噁唑硼烷为催化剂, 将起始原料γ-氯乙酰乙酸乙酯不对称催化氢化还原成(R)-γ-氯-β-羟基丁酸乙酯, 这一步的化学收率和光学收率都较高. 然后将(R)-γ-氯-β-羟基丁酸乙酯转化为盐酸L-肉碱和盐酸乙酰L-肉碱. 合成盐酸L-肉碱只需两步, 总收率为68.3%, ee值可达94.6%; 合成盐酸乙酰L-肉碱需三步, 总收率为62.6%, ee值可达96.8%. 还考察了反应温度、催化剂及还原剂的量等因素对γ-氯乙酰乙酸乙酯的不对称氢化还原的化学产率和光学收率的影响.

关键词: 乙酰L-肉碱, 手性噁唑硼烷, 不对称还原, 盐酸L-肉碱

The enantioselective synthesis of L-carnitine and acetyl-L-carnitine hydrochlorides was de-scribed. The asymmetric reduction of ethyl γ-chloroacetoacetate catalyzed by chiral oxazaborolidines enantioselectively gave ethyl R-3-hydroxy-4-chlorobutyrate in good yield and enantioselectivity. In following two steps, such an ester was converted into L-carnitine hydrochloride in 68.3% overall yield with 94.6% ee and acetyl-L-carnitine hydrochloride in 62.6% overall yield with 96.8% ee. Some factors effecting the yield and the enantioselectivity of asymmetric reduction of ethyl γ-chloroacetoacetate were investigated.

Key words: acetyl-L-carnitine, chiral oxazaborolidine, asymmetric reduction, L-carnitine hydrochloride