Method for producing...

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 209/52 (2006.01) A61K 31/40 (2006.01) C07B 37/10 (2006.01)

Patent

CA 2347757

The invention relates to a method for producing (+)-exo-6-phenyl-3--azabicyclo- [3.2.0]heptanes of formula (I) in which R represents hydrogen, chlorine, bromine, fluorine or methoxy. The inventive compounds are characterized in that a bisallyl ammonium salt of formula (II), in which R has the above-mentioned meanings and X- represents an anion, is photo-cyclized in an inert solvent while adding a sensitizer in a glass apparatus, and the selected (+)-exo-isomer (I) is precipitated as ditoluoyl tartrate using (-)-ditoluoyl tartaric acid from the obtained mixture, and this ditoluoyl tartrate is optionally recrystallized out of an alcohol/water mixture.

L'invention concerne un procédé de production de (+)-exo-6-phényl-3-azabicyclo-[3.2.0]heptanes correspondant à la formule (I), dans laquelle R représente hydrogène, chlore, brome, fluor ou méthoxy. Ce procédé se caractérise en ce que l'on photocyclise un sel de bisallylammonium correspondant à la formule (II), dans laquelle R a la signification susmentionnée et X<-> représente un anion, dans un solvant inerte, avec addition d'un sensibiliseur, dans un appareillage en verre, en ce que l'on fait précipiter, avec de l'acide (-)-ditoluoyltartrique, à partir du mélange obtenu, le (+)-exo-isomère (I) désiré, sous forme de tartrate de titoluoyle, et en ce que, éventuellement, on fait recristalliser cet isomère à partir d'un mélange alcool/eau.

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