tert-butyl 6-methyl-5-oxo-3,3a,4,5-tetrahydrocyclopenta[c]pyrrole-2(1H)-carboxylate → tert-butyl 4-methyl-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Participants

Reaction Steps

A mixture of tert-butyl 6-methyl-5-oxo-3,3a,4,5-tetrahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (11.6 g, 48.9 mmol), 20% palladium hydroxide on carbon (3.43 g) in methanol (30 mL) and dichloromethane (30.0 mL) was stirred under 20 psi hydrogen for 3 h. The mixture was then filtered to remove the solid catalyst. The filtrate was concentrated. Silica gel chromatography, eluting with 5-60% ethyl acetate in hexanes, gave tert-butyl 4-methyl-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate as a 3 to 1 mixture of endo- and exo-isomers (10.7 g, 91% yield).

Provenance & Evidence