Optical resolution of narwedine-type compounds

C - Chemistry – Metallurgy – 07 – D

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C07D 491/08 (2006.01) C07D 491/10 (2006.01)

Patent

CA 2256380

A process for the asymmetric transformation of a racemic compound of formula (I) wherein R1 is H or a alkyl group having up to 20 carbon atoms, R2 is H, or an alkyl, aryl, alkaryl or aralkyl group having up to 20 carbon atoms, and X is H, a halogen atom, tert-butyl, or any other removable substituent, comprises reaction of racemic compound (I) with an enantiomerically-enriched acid HY*, wherein Y* is a chiral group, to form a diastereomeric salt of compound (I) having Y* as a counterion. The salt obtained can then be reduced to give enantiomerically-enriched galanthamine, or a derivative thereof.

Procédé de transformation asymétrique d'un composé racémique représenté par la formule (I) dans laquelle R<1> représente H ou un groupe alkyle possédant 20 atomes de carbone maximum, R<2> représente H ou un groupe alkyle, aryle, alcaryle ou aralkyle possédant 20 atomes de carbone maximum et X représente H, un atome d'halogène, tert-butyle ou tout autre substituant amovible, consistant à effectuer la réaction dudit composé racémique (I) avec un acide HY* enrichi par énantiomère, Y* représentant un groupe chiral, de manière à obtenir un sel diastéréomère du composé (I) possédant Y* en tant que contre-ion. On peut ensuite réduire le sel obtenu afin de préparer galanthamine enrichie par énantiomère, ou un de ses dérivés.

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