A facile synthesis of cis-1-methyl-1,2,3,3a,4,8b- hexahydropyrrolo[3,2-f]pyrindine, an annulated nicotine analog.

[reaction: see text] The title compound, 2, has been synthesized in 45% overall yield in six steps from 3-bromopyridine. The hexahydropyrrolo[3,2-f]pyrindine skeleton was constructed from key intermediate 5, via intramolecular azomethine ylide-alkene [3 + 2] cycloaddition. The present work constitutes a general method for rapid assembly of other related tricyclic nicotine analogues.