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

Participants

Reaction Steps

A solution of benzyl (3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate (850 mg, 3.3 mmol) in THF (10 mL) was added dropwise to a suspension of lithium borohydride (86 mg, 4 mmol) in THF (5 mL) at −78° C. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The reaction mixture was then cooled to 0° C. and quenched with H2O2 (30% in H2O) and then poured onto H2O. The aqueous layer was extracted with EtOAc (2×) and the combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to obtain benzyl (3aR,6aS)-6-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (850 mg, 99%) as a colorless oil. LC/MS m/z 262.1 [M+H]+.

Provenance & Evidence