Chemoenzymatic Protocol for the Synthesis of Enantiopure β-Blocker (S)-Bisoprolol
Peer reviewed, Journal article
Published version
Permanent lenke
https://hdl.handle.net/11250/3098034Utgivelsesdato
2023Metadata
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- Institutt for kjemi [1404]
- Publikasjoner fra CRIStin - NTNU [38688]
Originalversjon
10.3390/catal13010054Sammendrag
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.