Patent ID: 6784319
Filing Date: 2004-08-31
Classification: C07C,C07F

Abstract:
A method for synthesizing a (Â±)-cis-2-((dimethylamino)methyl)-1-(aryl) cyclohexanol and a (Â±)-trans-2-((dimethylamino)methyl)-1-(aryl)cyclohexanol in a ratio of at least about 85:15, comprising the steps of:(a) contacting (1) a composition comprising (Â±)-2-((dimethylamino)methyl) cyclohexanone, a transition metal-salt, and an organic solvent and (2) an aryl organometallic compound to provide a (Â±)-cis-2-((dimethylamino)methyl)-1-(aryl)cyclohexoxide salt and a (Â±)-trans-2-((dimethylamino)methyl)-1-(aryl)cyclohexoxide salt in a ratio of at least about 85:15; and (b) protonating the (Â±)-cis-2-((dimethylamino)methyl)-1-(aryl)cyclohexoxide salt and (Â±)-trans-2-((dimethylamino)methyl)-1-(aryl)cyclohexoxide salt, wherein aryl is a phenyl or naphthyl group optionally substituted with one or more R1 groups; R1 is selected from C1-C10 straight or branched chain alkyls, â€”OR2, halogen, â€”CF3, â€”NH2, NHR2, NR2R2; and each R2 is independently a phenyl, benzyl or C1-C10 straight or branched alkyl group.