benzyl (3aR,6aS)-6-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate → (3aS,6aR)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-ol

Participants

Reaction Steps

A mixture of benzyl (3aR,6aS)-6-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (850 mg, 3.3 mmol) and Pd/C (200 mg) in THF (5.000 mL) was hydrogenated at 25-30 psi in a Parr shaker. After 12 h, the reaction mixture was diluted with MeOH and filtered through a plug of celite. The solvents were removed under reduced pressure to obtain (3aS,6aR)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-ol in quantitative yield.

Provenance & Evidence