The reaction of anhydroecgonine methyl ester (I) with 4-methylphenylmagnesium bromide (II) in ethyl ether gives 3beta-(4-methylphenyl)tropane-2beta-carboxylic acid methyl ester (III), which is demethylated by reaction with 2,2,2-trichloroethyl chloroformate (IV) yielding the carbamate (V), followed by reduction with Zn/AcOH to afford the nortropane derivative (VI). The alkylation of (VI) with the tributylstannane (VII), TEA and iodine in ethanol provides the adduct (VIII), which is finally brominated with NBS in THF.
By condensation of (-)-anhydroecgonine methyl ester (I) with 4-fluorophenylmagnesium bromide (II) by means of cuprous chloride in refluxing ether.