Process and diastereomeric salts useful for the optical...

Details Process and diastereomeric salts useful for the optical... Process and diastereomeric salts useful for the optical...

C - Chemistry, Metallurgy

07

D

C07D 211/22 (2006.01)

Patent

CA 2189000

A process and diastereomeric salts useful for the optical resolution of racemic a-[4-(1,1-dimethylethyl)phenyl]-4- (hydroxydiphenylmethyl)-1-piperidinebutanol, 4-[4-[4- (hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-.alpha.,.alpha.- dimethylbenzeneacetic acid and lower alkyl 4-[4-[4- (hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-.alpha.,.alpha.- dimethylbenzeneacetates. A process and diastereomeric salts useful for the optical resolution of compounds of the formula: Image wherein R is -CH3, -CO2H, or lower alkyl ester. The process comprises placing into solution a chiral resolving agent, either (+) / (-) -di-paratoluoyltartaric acid or (-) / (+) -mandelic acid, in an amount equimolar to a compound corresponding to the desired enantiomer of the above compound, precipitating the resulting diastereomeric salt between the chiral resolving agent and the target enantiomer and separating the enantiomer.

Procédé et sels diastéréomères utilisés pour effectuer la résolution optique d'acide alpha -[4-(1,1-diméthyléthyl)phényl]-4-(hydroxydiphénylméthyl)-1-pipéridinebutanol, 4-[4-[4-(hydroxydiphénylméthyl)-1-pipéridinyl]-1-hydroxybutyl]- alpha , alpha -acide diméthylbenzèneacétique racémique et 4-[4-[4-(hydroxydiphénylméthyl)-1-pipéridinyl]-1-hydroxybutyl]- alpha , alpha -diméthylbenzèneacétates d'alkyle inférieur. Ce procédé consiste à placer en solution un agent de résolution chiral, tel que de l'acide (+)/(-)-di-paratoluoyltartique ou de l'acide (-)/(+)-mandélique, selon une quantité équimolaire à un composé correspondant à l'énantiomère désiré du composé précité, à précipiter le sel diastomère résultant entre l'agent de résolution chiral et l'énantiomère cible puis à séparer l'énantiomère.

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