Alkylation of isoquinolone (I) with nitroethylene (II) in the presence of lithium diisopropylamide and ZnCl2 afforded nitroethyl compound (III). Reduction of nitro group with H2 and Raney Nickel proceeded with simultaneous cyclization to give the pyrroloisoquinoline (IV), which was then reduced with NaBH3CN to the corresponding pyrrolidine, predominantly with the cis stereochemistry. Resolution of enantiomers was accomplished by fractional recrystallization using di-p-toluoyltartaric acid.