rel-1,1-Dimethylethyl (3aR,6aS)-hexahydro-4-oxocyclopenta[c]pyrrole-2(1H)-carboxylate → HCID 86659849, compound

Participants

Reaction Steps

To a solution of (3aR,6aS)-tert-butyl 4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (4 g, 17.76 mmol), in tetrahydrofuran (30 mL) at 0° C. was added pyridinium bromide perbromide (6.62 g, 18.64 mmol). The mixture was stirred for 3 hours at room temperature, wherein an ice bath was needed to keep the mixture at about room temperature. The reaction mixture was quenched with 1 N NaHCO3 solution (80 mL) and 1 N sodium thiosulfate (20 mL). The mixture was stirred for 0.5 hours and extracted with ethyl acetate. The organic layer was separated and concentrated. The crude product was purified chromatographically using a 40 g silica gel cartridge and eluting with a gradient of 0-3% methanol/dichloromethane over 20 minutes to give (3aR,6aS)-tert-butyl 5-bromo-4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate: MS (ESI+) m/z 321 (M+NH4)+.

Provenance & Evidence