Synthesis and determination of the absolute stereochemistry of the enantiomers of adrafinil and modafinil

Antonio Osorio-Lozada; Thomas Prisinzano; Horacio F. Olivo

doi:10.1016/j.tetasy.2004.10.019

Synthesis and determination of the absolute stereochemistry of the enantiomers of adrafinil and modafinil

Antonio Osorio-Lozada, Thomas Prisinzano, Horacio F. Olivo

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

Abstract

Both enantiomers of modafinil, adrafinil, modafinic acid and ethyl modafinate were prepared from the diastereomers formed by reacting racemic β-sulfinyl carboxylic acid with (4R)-phenyl-thiazolidinethione. The absolute stereochemistry of the sulfoxide group was confirmed via X-ray analysis of one of the thiazolidinethione diastereomers.

Original language	English
Pages (from-to)	3811-3815
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	15
Issue number	23
DOIs	https://doi.org/10.1016/j.tetasy.2004.10.019
State	Published - Nov 29 2004

Bibliographical note

Funding Information:
Financial support for this work was provided by the National Science Foundation (CHE-0111292 and EEC-0310689). We thank Mr. John Podobinski for the preparation of compound 4 and Dr. Dale Swenson for obtaining the crystallographic analysis of compound (−)- 5 . We are indebted to Dr. Blake Watkins (University of Mississippi) for obtaining all the HRMS.

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/j.tetasy.2004.10.019

Cite this

@article{a1299f6d2c484c548a8807be1bb7c291,

title = "Synthesis and determination of the absolute stereochemistry of the enantiomers of adrafinil and modafinil",

abstract = "Both enantiomers of modafinil, adrafinil, modafinic acid and ethyl modafinate were prepared from the diastereomers formed by reacting racemic β-sulfinyl carboxylic acid with (4R)-phenyl-thiazolidinethione. The absolute stereochemistry of the sulfoxide group was confirmed via X-ray analysis of one of the thiazolidinethione diastereomers.",

author = "Antonio Osorio-Lozada and Thomas Prisinzano and Olivo, {Horacio F.}",

year = "2004",

month = nov,

day = "29",

doi = "10.1016/j.tetasy.2004.10.019",

language = "English",

volume = "15",

pages = "3811--3815",

number = "23",

}

TY - JOUR

T1 - Synthesis and determination of the absolute stereochemistry of the enantiomers of adrafinil and modafinil

AU - Osorio-Lozada, Antonio

AU - Prisinzano, Thomas

AU - Olivo, Horacio F.

PY - 2004/11/29

Y1 - 2004/11/29

N2 - Both enantiomers of modafinil, adrafinil, modafinic acid and ethyl modafinate were prepared from the diastereomers formed by reacting racemic β-sulfinyl carboxylic acid with (4R)-phenyl-thiazolidinethione. The absolute stereochemistry of the sulfoxide group was confirmed via X-ray analysis of one of the thiazolidinethione diastereomers.

AB - Both enantiomers of modafinil, adrafinil, modafinic acid and ethyl modafinate were prepared from the diastereomers formed by reacting racemic β-sulfinyl carboxylic acid with (4R)-phenyl-thiazolidinethione. The absolute stereochemistry of the sulfoxide group was confirmed via X-ray analysis of one of the thiazolidinethione diastereomers.

UR - http://www.scopus.com/inward/record.url?scp=9644279575&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=9644279575&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2004.10.019

DO - 10.1016/j.tetasy.2004.10.019

M3 - Article

AN - SCOPUS:9644279575

SN - 0957-4166

VL - 15

SP - 3811

EP - 3815

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 23

ER -

Synthesis and determination of the absolute stereochemistry of the enantiomers of adrafinil and modafinil

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this