Applications of electrophilic molecular rearrangement to the synthesis of NN-dimethylphenylalanine and benzo[b]quinolizidine

Abstract

The quaternary ion (Ia), from benzyldimethylamine and ethyl chloroacetate, gave, by treatment with potassium t-butoxide followed by hydrolysis, a moderate yield of NN-dimethyl-3-phenylalanine. Phenyl-lithium effected an analogous rearrangement of the ion (VI), from αα′-dibromo-o-xylene and 1,2,5,6-tetrahydropyridine, giving by expansion of the five-membered ring a product hydrogenated to benzo[b]quinolizidine (VII).