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

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)+.

1. customat about room temperature
2. customThe reaction mixture was quenched with 1 N NaHCO3 solution (80 mL) and 1 N sodium thiosulfate (20 mL)
3. stirringThe mixture was stirred for 0.5 hours
4. extractionextracted with ethyl acetate
5. customThe organic layer was separated
6. concentrationconcentrated
7. customThe crude product was purified chromatographically
8. washeluting with a gradient of 0-3% methanol/dichloromethane over 20 minutes

ORD record

ord-7961145ce26147bc800b8122478a22bd

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796470B2