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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.51B [2012] >
IJC-B Vol.51B(10) [October 2012] >
| 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
Resolution
Lipase
Cinchonidine |
| 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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