Article ID Journal Published Year Pages File Type
39216 Applied Catalysis A: General 2015 7 Pages PDF
Abstract

•A straightforward chemoenzymatic synthesis of rasagiline mesylate has been developed.•The key steps involved kinetic lipase-mediated resolution and Mitsunobu reaction.•T. lanuginosus was robust biocatalyst afforded S-indanol with e.e. > 99% in 15 min.•Immobilized T. lanuginosus could be effectively reused in ten reaction cycles.

A straightforward chemoenzymatic synthesis of rasagiline mesylate has been developed. The key steps for the introduction of chirality involved kinetic enzymatic resolution with lipases via acetylation of rac-indanol and an inversion configuration Mitsunobu reaction of the produced (S)-indanol. Immobilized lipase from Thermomyces lanuginosus proved to be a robust biocatalyst in the kinetic resolution, leading to (S)-indanol with high selectivity (e.e. > 99%, E > 200) in just 15 min, at 35 °C, in hexane, being reused for ten-times without significant loss of the activity and selectivity.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (129 K)Download as PowerPoint slide

Related Topics
Physical Sciences and Engineering Chemical Engineering Catalysis
Authors
, , , , , ,