Sodium triacetoxyborohydride → (1-{4-[8-(3-fluoro-azetidin-1-ylmethyl)-4-oxo-2-phenyl-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

A solution of {1-[4-(8-formyl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (81 mg, 0.163 mmol) and 3-fluoroazetidine hydrochloride (23 mg, 0.245 mmol) in dichloroethane (5 mL) was stirred for 10 min. Sodium triacetoxyborohydride (87 mg, 0.409 mmol) was added and the reaction stirred at RT for 18 h. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution, diluted with DCM, filtered through a phase separation cartridge and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 50% EtOAc in DCM) to give the title compound as a gummy solid. LCMS (Method G): RT=2.71 min, [M+H]+=555.

Provenance & Evidence