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Title: <span style="font-size:12.0pt;font-family: "Times New Roman";mso-fareast-font-family:"Times New Roman";mso-ansi-language: EN-GB;mso-fareast-language:EN-US;mso-bidi-language:AR-SA" lang="EN-GB">Eco-friendly, industrial process for synthesis of (<i style="mso-bidi-font-style:normal">S</i>)-3-(aminomethyl)-5-methylhexanoic acid [pregabalin]</span>
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, (<i style="mso-bidi-font-style:normal">RS</i>)-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 (<i style="mso-bidi-font-style:normal">S</i>)-ethyl-3-cyano-5-methylhexanoate (>99% <i style="mso-bidi-font-style:normal">ee</i>, 85% yield) or resolution <i style="mso-bidi-font-style:normal">via </i>diastereomeric salt formation with cinchonidine to obtain optically pure (<i style="mso-bidi-font-style: normal">S</i>)-3-cyano-5-methyl-hexanoic acid (>99% <i style="mso-bidi-font-style:normal">ee</i>, 85% yield), which has been subsequently converted to pregabalin (>99% <i style="mso-bidi-font-style: normal">ee</i>). In addition, for improvement of atom economy as well as cost effectiveness, an efficient process for complete racemization of (<i style="mso-bidi-font-style:normal">R</i>)-3-cyano-5-methyl-hexanoic acid has been developed.
Description: 1470-1488
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.51B(10) [October 2012]

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