An enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid via asymmetric hydrogenation.
J Org Chem
; 68(14): 5731-4, 2003 Jul 11.
Article
em En
| MEDLINE
| ID: mdl-12839471
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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Base de dados:
MEDLINE
Assunto principal:
Ácido gama-Aminobutírico
/
Anticonvulsivantes
Idioma:
En
Ano de publicação:
2003
Tipo de documento:
Article