Enantioenriched synthesis of Escitalopram using lithiation-borylation methodology

Benjamin M. Partridge, Stephen P. Thomas, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

12 Citations (Scopus)

Abstract

The asymmetric synthesis of Escitalopram has been completed using a lithiation-borylation reaction as the key step. Suitably functionalized enantioenriched carbamate (er 98:2) and boronic ester coupling partners were prepared and following deprotonation with s-BuLi and borylation, the tertiary alcohol was obtained in 42% yield and 93:7 er. The lithiation-borylation reaction was found to tolerate nitrile, benzylic alcohol and N-Boc functionalities. The tertiary alcohol was converted to Escitalopram in three further steps. (C) 2011 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)10082-10088
Number of pages7
JournalTetrahedron
Volume67
Issue number52
DOIs
Publication statusPublished - 30 Dec 2011

Keywords

  • Lithiation-borylation
  • Escitalopram
  • Total synthesis
  • Carbamate
  • Boronic ester
  • ENANTIOSELECTIVE ADDITION
  • SECONDARY ALCOHOLS
  • BORONIC ESTERS
  • CONVERSION
  • ALDEHYDES
  • RESOLUTION

Cite this