Triacetoxyperiodinane → tert-butyl N-[5-[(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-2-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate

Participants

Reaction Steps

A solution of tert-butyl N-[5-[(3aR,6aS)-6-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (104 mg, 0.18 mmol) in DCM (1 mL) at 0° C. was treated with a solution of Dess-Martin periodinane (921 μL 0.3 M, 0.28 mmol) in DCM. The reaction mixture was warmed to room temperature and stirred overnight. The solvent was evaporated under reduced pressure and the crude material was purified by silica gel column chromatography using 5-60% EtOAc in DCM to yield tert-butyl N-[5-[(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-2-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (57 mg, 55%) as a yellow solid. LC/MS m/z 463.5 [M+H-Boc]+.

Provenance & Evidence