4-Nitrophenyl chloroformate → HCID 22725139, compound

Participants

Reaction Steps

To a well stirred solution of (+)-5-methoxycarbonyl-1,6-dihydro-2-methoxy-4-methoxymethyl-6-(3,4-difluorophenyl)pyrimidine (1.167 g, 3.576 mmol) and 4-(N,N-dimethylamino)pyridine (0.655 g, 5.364 mmol) in CH2Cl2 (20 mL) was added powdered 4-nitrophenyl chloroformate (0.937 g, 4.65 mmol) at room temperature. Solvent was evaporated and the residue was purified by column chromatography on silica gel using hexanes/EtOAc (7/3%) as the eluent to give (−)-5-methoxycarbonyl-4-methoxymethyl-1,6-dihydro-2-methoxy-6-(3,4-diflurophenyl)-1-[(4-nitrophenyloxy)carbonyl]pyrimidine (1.761 g, 100%) as a viscous oil. [α]D=−335.3 (c=1.0 g in 100 mL CHCl3).

Provenance & Evidence