The Synthesis of Pyrrolidine-Substituted Nicotine Analogs

As part of a program to synthesize nicotine homologs and analogs, the potentially versatile condensation of 3-pyridyl lithium with a 1-pyrroline-1-oxide (cyclic nitrone) has been studied. The product, an N-hydroxynornicotine derivative, was obtained in moderate yield and could be converted by way of the corresponding myosmine and nornicotine compounds to the desired gemdimethylnicotine homolog. Spectral characteristics of these and certain side products are reported.