Trifluoroacetic acid → benzyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Steps

Into a 50 mL roundbottom flask, was placed tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (3.5 g, 10.00 mmol). To this was added dichloromethane (20 mL) followed by the addition of trifluoroacetic acid (5 mL). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at room temperature. The mixture was concentrated by evaporation under vacuum using a rotary evaporator. This was followed by the addition of dichloromethane (20 mL). This was followed by the addition of triethylamine (3.03 g, 29.94 mmol). To the mixture was added benzyl chloroformate (2.05 g, 12.02 mmol). The resulting solution was allowed to react overnight at room temperature. The reaction mixture was filtered and the filtrate was concentrated under vacuo. The crude mixture was purified by silica gel chromatography (1:40 EtOAc/petroleum ether) to yield the title compound as a yellow liquid.

Provenance & Evidence