Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol-Reference-Cited by-同舟云学术

Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol

Published:2022-12-27 Issue:1 Volume:13 Page:54
ISSN:2073-4344
Container-title:Catalysts
language:en
Short-container-title:Catalysts

Author:

Bocquin Lucas,Jacobsen Elisabeth Egholm^ORCID

Abstract

The β-blocker (S)-bisoprolol hemifumarate has been synthesised in 96% enantiomeric excess with 19% total yield in a six-step synthesis. A transesterification reaction of the racemic chlorohydrin 1-chloro-3-(4-((2-isopropoxyethoxy)methyl)phenoxy)propan-2-ol catalysed by lipase B from Candida antarctica resulted in the R-chlorohydrin in high enantiomeric purity. Reaction of this building block with isopropylamine in methanol gave (S)-bisoprolol, and further reaction with fumaric acid gave (S)-bisoprolol fumarate in 96% ee. Specific rotation value confirmed the absolute configuration of the enantiopure drug.

Publisher

MDPI AG

Subject

Physical and Theoretical Chemistry,Catalysis,General Environmental Science

Link

https://www.mdpi.com/2073-4344/13/1/54/pdf

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