New asymmetric process for the preparation of...

Details New asymmetric process for the preparation of... New asymmetric process for the preparation of...

C - Chemistry, Metallurgy

07

D

C07D 241/04 (2006.01) A61K 31/496 (2006.01) A61P 25/04 (2006.01) C07C 237/32 (2006.01) C07D 215/12 (2006.01) C07D 307/79 (2006.01) C07D 401/06 (2006.01) C07D 401/14 (2006.01) C07D 403/14 (2006.01) C07D 405/06 (2006.01) C07D 405/12 (2006.01) C07D 405/14 (2006.01) C07D 409/06 (2006.01) C07D 409/12 (2006.01) C07D 409/14 (2006.01)

Patent

CA 2440104

An asymmetric synthesis of diarylmethylpiperazines is described. The synthetic route enables preparation of a variety of enatiomerically pure amines with different N-alkyl groups. The invention includes an asymmetric addition of organometallic compounds to chiral sulfinimine to give adducts in predominantly one diastereomer can subsequently be transferred into pure enantiomers of by cleavage of the chiral auxilliary which is followed by synthesis of the piperazine ring by alkylation procedures.

L'invention concerne une synthèse asymétrique de diarylméthylpipérazines. La voie synthétique permet de préparer une variété d'amines énantiomériquement pures avec différents groupes <I>N</I>-alkyle. L'invention consiste à ajouter, de manière asymétrique, des composés organométalliques à une sulfinimine chirale pour donner des adduits essentiellement dans un diastéréomère. Après purification par chromatographie ou cristallisation, le diastéréomère pur peut ensuite être transféré dans des énantiomères purs par clivage de l'auxiliaire chiral, suivi de la synthèse d'un anneau de pipérazine, à l'aide de procédures d'alkylation.

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