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

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

doi:10.1016/j.tetasy.2004.01.039

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

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

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52 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 language	English
Pages (from-to)	1053-1058
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	15
Issue number	6
DOIs	https://doi.org/10.1016/j.tetasy.2004.01.039
State	Published - 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

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10.1016/j.tetasy.2004.01.039

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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.",

author = "Thomas Prisinzano and John Podobinski and Kevin Tidgewell and Min Luo and Dale Swenson",

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AU - Prisinzano, Thomas

AU - Podobinski, John

AU - Tidgewell, Kevin

AU - Luo, Min

AU - Swenson, Dale

N1 - 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.

PY - 2004/3/22

Y1 - 2004/3/22

N2 - 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.

AB - 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.

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

Abstract

Bibliographical note

ASJC Scopus subject areas

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