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Citation: SONG Guang-Wei, ZHU Jin-Tao, YAO Guo-Xin, CHEN Gang. Asymmetric Synthesis of (S)-Metoprolol[J]. Chinese Journal of Applied Chemistry, ;2010, 27(11): 1286-1290. doi: 10.3724/SP.J.1095.2010.90880 shu

Asymmetric Synthesis of (S)-Metoprolol

Department of Chemistry, Zhejiang Science-Technology University, Hangzhou 310018

Received Date: 25 December 2009
Revised Date: 19 March 2010

Enantioenriched(S)-3-chloro-1,2-propanediol and(R)-epichlorohydrin were obtained from the kinetic hydrolysis resolution of racemic epichlorohydrin by(S,S)-salen Co(Ⅲ) OAc.(S)-Metoprolol with optical purity higher than 99% could be prepared via the reaction of 4-(2-methoxyethyl) phenol with(S)-3chloro-1,2-propanediol followed by an amination reaction using isopropyl amine.When (R)-epichlorohydrin was used as the chiral precursor,(S)-metoprolol could be also prepared but with less optical purity(>92%). The overall yield of(S)-metoprolol was 53.9%.The structure of the product was determined by IR,¹H NMR,¹³C NMR and MS.This procedure is effective,simple and has a high utilization rate of raw material.The optical purity and yield of the product are satisfactory.The process is promising for scaling-up industrial potential applications.
- (S)-metoprolol,
- racemic epichlorohydrin,
- catalyzed hydrolysis resolution,
- (R)-epichlorohydrin,
- (S)-chloropropanediol,
- asymmetric synthesis
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