Ethyl 3 alpha-phenyltropane-3 beta-carboxylate and related compounds

3 alpha-Phenyl-3 beta-tropanyl phenyl ketoxime furnished 3 alpha-phenyltropane-3 beta-carboxylic acid which on esterification gave the ethyl ester XV, the tropane analog of meperidine (1). The ketobemidone analog XXI was prepared from a-ecgonine amide by successive treatment with ethylmagnesium bromide and m-anisylmagnesium bromide, followed by treatment of the resulting diol with zinc chloride-acetic anhydride and then demethylation. Ethyl 3 alpha-phenyltropane-3 beta-carboxylate (XV) was slightly more potent than meperidine as an analgesic.