1-Methylpyrrolidine → Prop-1-en-2-yl 5-(trifluoromethyl)pyridin-3-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

5-(trifluoromethyl)pyridin-3-amine (883 mg, 5.45 mmol) was suspended in dry THF (20 mL) and N-methylpyrrolidine (680 μL, 6.54 mmol) was added to give a brown suspension. The mixture was cooled to 0° C. and isopropenyl chloroformate (715 μL, 6.54 mmol) was added dropwise over 15 min. The suspension was allowed to reach RT and was stirred for 4 h. EtOAc (60 mL) and H2O (10 mL) were added and the organic layer was isolated, washed with 50% brine (10 mL), dried (MgSO4), filtered and evaporated to leave a brown oil, which solidified upon standing (1.05 g). The solid was taken up in CH2Cl2 (4 mL) and purified by column chromatography on silica gel, eluting with EtOAc in CH2Cl2 (6%→40%), to give a white solid. Yield: 600 mg (45%).

Provenance & Evidence