Synthesis and determination of the absolute configuration of the enantiomers of modafinil

Thomas Prisinzano, John Podobinski, Kevin Tidgewell, Min Luo, Dale Swenson

Research output: Contribution to journalArticlepeer-review

56 Scopus citations

Abstract

The asymmetric synthesis of both enantiomers of modafinil, a unique CNS stimulant with a reduced abuse liability, is described. This approach effectively prepares modafinil on a multigram scale in several steps from benzhydrol. The described synthetic route has also been used to produce the more water soluble analogue, adrafinil. X-ray crystallographic analysis on (-)-(diphenylmethanesulfinyl)acetic acid has determined the absolute configuration to be R.

Original languageEnglish
Pages (from-to)1053-1058
Number of pages6
JournalTetrahedron Asymmetry
Volume15
Issue number6
DOIs
StatePublished - Mar 22 2004

Bibliographical note

Funding Information:
The authors thank the College of Pharmacy and the Biological Sciences Funding Program of The University of Iowa for financial support of this work.

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis and determination of the absolute configuration of the enantiomers of modafinil'. Together they form a unique fingerprint.

Cite this