Pyridine → HCID 117833033, compound

Participants

Reaction Steps

Triphosgene (1.33 g, 4.48 mmol) was added in several portions to a dichloromethane solution (50 ml) of 1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (1.87 g, 11.2 mmol) and pyridine (2.3 ml, 28 mmol) under ice-cooled condition. After stirring the mixture for 30 min under ice-cooled condition, tert-butanol (2.2 ml, 22.4 mmol) was dropped, and the mixture was stirred for 8 h. The reaction was stopped by adding water to the reaction liquid. The reaction liquid was then extracted with diethyl ether, washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and N-tert-butoxycarbonyl-1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (0.37 g, 13%), and 1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (1.1 g, 59%) were collected. The collected 1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one was subjected to the same procedure twice to give N-tert-butoxycarbonyl-1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (1.36 g, 44%).

Provenance & Evidence