Preparation of optically pure beta-amino acids having...

Details Preparation of optically pure beta-amino acids having... Preparation of optically pure beta-amino acids having...

C - Chemistry, Metallurgy

07

D

C07D 295/14 (2006.01) C07C 227/20 (2006.01) C07C 227/32 (2006.01) C07C 229/08 (2006.01) C07C 229/30 (2006.01) C07C 233/47 (2006.01)

Patent

CA 2602418

Disclosed are materials and methods for preparing optically active .beta.- amino acids, which bind to the alpha-2-delta subunit of a calcium channel and are useful for treating pain, fibromyalgia, and a variety of psychiatric and sleep disorders. The method includes reacting a chiral allyl amine with a 2- alkynoate in the presence of a Lewis acid and a base to give a chiral tertiary enamine, which after reaction with ammonia, is hydrogenated to give optically active .beta.-amino acids.

Cette invention concerne des matériaux et des procédés permettant de préparer des ß-amino acides optiquement purs, lesquels se lient à la sous-unité alpha-2-delta d'un canal calcique et sont utilisés pour traiter la douleur, la fibromyalgie, ainsi qu'une large gamme de troubles psychiatriques et de troubles du sommeil. Le procédé décrit dans cette invention consiste à faire réagir une amine allyle chirale avec un 2-alkynoate en présence d'un acide de Lewis et d'une base pour obtenir une énamine tertiaire chirale, laquelle, après réaction avec l'ammoniac, est hydrogénée pour produire des ß-amino acides optiquement purs.

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