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Title: Eco-friendly, industrial process for synthesis of (S)-3-(aminomethyl)-5-methylhexanoic acid [pregabalin]
Authors: Roy, Bhairab Nath
Singh, Girij Pal
Lathi, Piyush Suresh
Agrawal, Manoj Kunjabihari
Keywords: Pregabalin
Cyano mono ester
Issue Date: Oct-2012
Publisher: NISCAIR-CSIR, India
Abstract: In the present work pregabalin has been synthesized by four novel routes, which have been broadly categorized into two approaches. In the first strategy, it has been synthesized through a hemiaminal intermediate. In the second approach, (RS)-ethyl-3-cyano-5-methylhexanoate, a key intermediate, has been synthesized through novel and cost effective routes, followed by either lipase catalyzed kinetic resolution to optically pure (S)-ethyl-3-cyano-5-methylhexanoate (>99% ee, 85% yield) or resolution via diastereomeric salt formation with cinchonidine to obtain optically pure (S)-3-cyano-5-methyl-hexanoic acid (>99% ee, 85% yield), which has been subsequently converted to pregabalin (>99% ee). In addition, for improvement of atom economy as well as cost effectiveness, an efficient process for complete racemization of (R)-3-cyano-5-methyl-hexanoic acid has been developed.
Page(s): 1470-1488
CC License:  CC Attribution-Noncommercial-No Derivative Works 2.5 India
ISSN: 0975-0983(Online); 0376-4699(Print)
Source:IJC-B Vol.51B(10) [October 2012]

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