Citation: Shan Zhen He, Xue Ming Li, Jia Dai, Ming Yan. Synthesis of antidepressant duloxetine via asymmetric transfer hydrogenation[J]. Chinese Chemical Letters, ;2008, 19(1): 23-25. doi: 10.1016/j.cclet.2007.10.046 shu

Synthesis of antidepressant duloxetine via asymmetric transfer hydrogenation

Shan Zhen He ^a,b, ,
Xue Ming Li ^a ,
Jia Dai ^a ,
Ming Yan ^a

a The Industrial Institute of Fine Chemicals and Synthetic Drugs, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510080, China;
b Guangdong Provincial People's Hospital, Guangzhou 510060, China

Received Date: 26 August 2007

Fund Project: We thank the National Natural Science Foundation of China(No.20472061), Guangzhou Bureau of Science and Technology for financial support of this study.

Antidepressant duloxetine (1) was prepared via asymmetric transfer hydrogenation of 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one (3). The Ru(Ⅱ), Rh(Ⅲ) and Ir(Ⅲ) complexes of several chiral ligands were examined as the catalyst and (S,S)-N-tosyl-1,2-diphenyl ethylenediamine (TsDPEN)-Ru(Ⅱ) complex was found to provide good yield and excellent enantios-electivity.
- Duloxetine,
- Synthesis,
- Asymmetric transfer hydrogenation,
- TsDPEN-Ru(Ⅱ) complex
1. [1]
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3. [3]
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7. [7]
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