Enantioselective synthesis of (-)-(R) Silodosin by ultrasound-assisted diastereomeric crystallization

Indrajeet J. Barve, Li Hsun Chen, Patrick C.P. Wei, Jui Te Hung, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Enantioselective synthesis of clinically approved drug - Silodosin for the treatment of benign prostatic hyperplasia from the commercially available compounds 1-acetyl-5-(2-aminopropyl) indoline-7-carbonitrile A and 2-(2-(2,2,2-trifluoroethoxy)phenoxy)ethyl methanesulfonate C is explored. Key step in the synthesis is chiral resolution of intermediate 1, which was achieved by a simple diastereomeric crystallization using (S)-(+)-mandelic acid assisted by ultrasonication. The present synthetic strategy has lesser number of steps and is vastly improved the overall yield in this short route towards target compound - Silodosin.

Original languageEnglish
Pages (from-to)2834-2843
Number of pages10
JournalTetrahedron
Volume69
Issue number13
DOIs
StatePublished - 1 Apr 2013

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