Process for the preparation of 6,6-dimethyl-3-azabicyclo-[3.1.0]- hexane compounds utilizing bisulfite intermediate
AssigneeSchering Corporation
InventorsThierry Berranger, Patrice Demonchaux
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Abstract
The present invention provides for a process for preparing 6,6-Dimethyl-3-aza-bicyclo[3.1.0]hexane-2-sulfonate, an intermediateuseful in the efficient preparation of (1R,2S,5S)-methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylic acid and esters and salts thereof, processes for preparing (1R,2S,5S)-methyl 6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylic acid and esters and salts thereof from the sulfonate intermediate and processes for preparing 6,6-Dimethyl-3-aza-bicyclo[3.1.0]hexane-2-sulfonate.
Claims17
A process for preparing a mixture of 6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-sulfonate sodium adduct compounds of Formulae Va-S and Vb-S,
- the process comprising reacting an organic solution of a imine mixture of compounds Formulae Va and Vb
- with a source of sodium bisulfite.
(canceled)
(canceled)
A process for the provision of a mixture of nitrile compounds of Formulae VIa and VIb,
- the process comprising:
- (i) reacting caronic anhydride with benzylamine to form the 2,4 dione of formula IIb
- (ii) reducing the dione of Formula IIB to the 3-aza-benzyl-bicyclohexane compound of Formula IIC;
- (iii) reducing the compound of Formula IIC to 6,6-Dimethyl-3-aza-bicyclo[3.1.0]hexane;
- (iv) oxidizing the hexane product from reducing Step (iii) provide a mixture comprising the imines of Formulae Va and Vb:
- (v) reacting the mixture of compounds produced in oxidizing step (iv) with sodium bisulfite to provide the trans-bisulfite adduct compounds of Formula Va-S and Vb-S;
- (vi) reacting the mixture of bisulfite adduct compounds produced in Step (v) with a source of cyano adduct to form the corresponding mixture of the nitrile compounds of Formula VIa and VIb;
(canceled)
The compound of Formula Va-S
The Compound of Formula Vb-S
Dependencies are inferred from the claim text.