C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 211/42 (2006.01) C07D 211/72 (2006.01) C07D 211/74 (2006.01) C07D 405/04 (2006.01)
Patent
CA 2318946
Disclosed is a method for producing (-)cis-3-hydroxy-1-methyl-4-(2,4,6- trimethoxyphenyl)-piperidine characterised in that 1-methyl-piperidine-4-one is converted into hydrobromide, subsequently transformed with bromine into 3(R.S)-bromine-1-methyl-4-oxo-piperidine-hydrobromide and reacted with 1.3,5-trimethoxybenzol to form 3(R,S)-bromine-1-methyl-4-(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydro-pyridine- hydrobromide. By stirring the reaction solution into an organic solvent, 3(R,S)-bromine-1-methyl-4-(2,4,6- trimethoxyphenyl)-1,2,3,6-tetrahydro-pyridine-hydrobromide is initially isolated as a solid and subsequently the product is mixed with water and converted into 3(R,S)-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-1,2,3,6-tetrahydro-pyridine by means of stirring. The product thus prepared is catalytically hydrogenated into a racemic 3,4-cis-alcahol and subsequently, enantiomerically pure (-)cis-3-hydroxy-1-methyl-4-(2,4,6-trimethoxyphenyl)-piperidine is obtained by separation of racemic mixtures with chiral auxiliary reagents from racemic 3,4-cis alcohol.
L'invention concerne un procédé de production de (-)cis-3-hydroxy-1-méthyl-4-(2,4,6-triméthoxyphényl)-pipéridine qui se caractérise en ce que l'on convertit de la 1-méthyl-pipéridin-4-one en bromhydrate que l'on transforme ensuite avec du brome en 3(R,S)-bromo-1-méthyl-4-oxo-pipéridine-bromhydrate que l'on transforme encore avec du 1,3,5-triméthoxybenzol en 3(R,S)-bromo-1-méthyl-4-(2,4,6-triméthoxyphényl)-1,2,3,6-tétrahydro-pyridine-bromhydrate. Par délayage de la solution de réaction dans un solvant organique on isole d'abord, comme matière solide, du 3(R,S)-bromo-1-méthyl-4-(2,4,6-triméthoxyphényl)-1,2,3,6-tétrahydro-pyridine-bromhydrate, puis l'on mélange le produit obtenu avec de l'eau et on le transforme, par agitation, en 3(R,S)-hydroxy-1méthyl-4-(2,4,6-triméthoxyphényl)-1,2,3,6-tétrahydropyridine. Le produit ainsi préparé est hydrogéné catalytiquement en 3,4-cis-alcool racémique et l'on obtient la (-)cis-3-hydroxy-1-méthyl-4-(2,4,6-triméthoxyphényl)pipéridine énantiomériquement pur par dissociation des racémates avec des réactifs auxiliaires, à partir du 3,4-cis-alcool racémique.
Breipohl Gerhard
Michalowsky Jurgen
Aventis Pharma Deutschland Gmbh
Bereskin & Parr Llp/s.e.n.c.r.l.,s.r.l.
Sanofi-Aventis Deutschland Gmbh
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