An enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid via asymmetric hydrogenation - PubMed (original) (raw)
. 2003 Jul 11;68(14):5731-4.
doi: 10.1021/jo034397b.
Pieter D De Koning, Todd M Grote, Marvin S Hoekstra, Garrett Hoge, Rex A Jennings, William S Kissel, Tung V Le, Ian C Lennon, Thomas A Mulhern, James A Ramsden, Robert A Wade
Affiliations
- PMID: 12839471
- DOI: 10.1021/jo034397b
An enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid via asymmetric hydrogenation
Mark J Burk et al. J Org Chem. 2003.
Abstract
A concise enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid (1, Pregabalin) has been developed. The key step is the asymmetric hydrogenation of a 3-cyano-5-methylhex-3-enoic acid salt 2 with a rhodium Me-DuPHOS catalyst, providing the desired (S)-3-cyano-5-methylhexanoate 3 in very high ee. Subsequent hydrogenation of the nitrile 3 with a heterogeneous nickel catalyst provides Pregabalin 1 in excellent overall yield and purity.
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