Abstract
Some 3, 4-epiminopyrrolidines were synthesized by two alternate methods. Lithium aluminum hydride reduction of N-(p-methoxyphenyl)-1-benzyl-2, 3-aziridinedicarboximide (6) afforded 1-(p-methoxyphenyl)-3, 4-(N-benzylepimino) pyrrolidine (8) in a low yield. Epoxidation of 1-benzoyl-△3-pyrroline (12) with pertrifloroacetic acid gave 1-benzoyl-3, 4-epoxypyrrolidine (13) which formed 1-benzoyl-trans-3-azido-4-mesyloxypyrrolidine (15) on successive treatment with sodium azide and mesyl chloride. 15 was converted into 1-benzyl-3, 4-epiminopyrrolidine (16) on treatment with lithium aluminum hydride, or into 1-benzoyl-3, 4-epiminopyrrolidine (20) with sodium borohydride and cobalt (II)-tris (α, α'-dipyridyl) bromide, respectively, in a fair yield. The nuclear magnetic resonance spectra of these compounds were evaluated.
