Hydrochloric Acid → HCID 86701854, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (3aR,8bS)-2,4-dioxo-3a,8b-dihydro-3H-indeno[1,2-b]pyrrole-1-carboxylate F 26 (1.60 g, 5.56 mmol) in ethanol (20 mL) and THF (20 mL) was added at 0° C. NaBH4 (0.316 g, 8.15 mmol). The solution was stirred for 2 h at 0° C. 1M HCl was carefully added and the solution was concentrated in vacuo. The residue was partitioned between ethyl acetate and water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by flash chromatography (2/1 cyclohexane/ethyl acetate) to give tert-butyl (3aR,4R,8bS)-4-hydroxy-2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate F27 (800 mg, 50%). LCMS (method E): 0.78 min; ES+: 601 (2M+Na+).

Provenance & Evidence