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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (07): 857-861. 上一篇    下一篇

研究论文

有机相酶催化拆分制备(S)-2-氯-1-(2-噻吩)-乙醇

徐刚，程咏梅，吴坚平，杨立荣*   

  1. (浙江大学材料与化学工程学院 杭州 310027)
  • 收稿日期:2006-12-21 修回日期:1900-01-01 发布日期:2007-06-30
  • 通讯作者: 杨立荣*

Preparation of (S)-2-(2-Chloro-1-hydroxyethyl)thiophene by Lipase-Catalyzed Resolution in Organic Phase

XU Gang,CHEN Yong-Mei,WU Jian-Ping,YANG Li-Rong*   

  1. (College of Material Science and Chemical Engineering, Zhejiang University, Hangzhou 310027)
  • Received:2006-12-21 Revised:1900-01-01 Published:2007-06-30
  • Contact: YANG Li-Rong*

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首次在有机相中对酶催化条件下的2-氯-1-(2-噻吩)-乙醇的反应进行了研究. 通过对不同来源酶的筛选, 找到了Novozym 435和Alcaligenes sp两种选择性较好的酶, 它们均对该反应具有较高的选择性和较快的反应速度, 在此基础上进一步通过对溶剂、温度、摇床转速以及酶用量的筛选, 确定了能够有效拆分2-氯-1-(2-噻吩)-乙醇的较佳反应条件. 当温度35 ℃, 酶量10 mg/mL, 反应72.5 h, 产物的ee值为98.5%时收率为48.6%.

关键词: 2-氯-1-(2-噻吩)-乙醇, 拆分, 度洛西汀, 酶催化

The kinetic resolution of 2-(2-chloro-1-hydroxyethyl)thiophene in organic phase, catalyzed by lipase, was firstly investigated. Through screening lipases, lipase Novozym 435 and lipase Alcaligenes sp were found to show higher activity and better enantioselectivity for the resolution of 2-(2-chloro- 1-hydroxyethyl)thiophene. The optimal reaction conditions were finally achieved by further investigating the effects of solvents, temperature, rotation speed and enzyme concentrations. 98.5% ee value of (S)-2- (2-chloro-1-hydroxyethyl)thiophene with 48.6% yield could be achieved after 72.5 h when the temperature was 35 ℃ and the concentration of lipase was 10 mg/mL.

Key words: duloxetine, resolution, lipase-catalyzed, (S)-2-(2-chloro-1-hydroxyethyl)thiophene