反应详情

tert-butyl 3-cyano-3-pyridin-2-ylazetidine-1-carboxylate (14.2 g, 55 mmol) in 1,2-dichloroethane (120 ml) was cooled in an ice-bath and treated with methyl triflate. The reaction was stirred at room temperature for 1 hour then at reflux overnight (no starting material in the solution). The resulting orange/brown precipitate was filtered off and washed with more 1,2-dichloroethane. The solid was then dissolved in ethanol (150 ml) and acetic acid (1.5 eq, 5.5 ml) was added. Platinum dioxide (1.5 g) was added and the reaction hydrogenated on a parr at 40 psi overnight. Tlc and mass spec showed complete conversion. The reaction was filtered under nitrogen and the filtrate was evaporated to dryness to give tert-Butyl 3-cyano-3-(1-methylpiperidin-2-yl)azetidine-1-carboxylate as an oil which was used without further purification. m/z (M++H) 280.

1. temperatureat reflux overnight (no starting material in the solution)
2. filtrationThe resulting orange/brown precipitate was filtered off
3. washwashed with more 1,2-dichloroethane
4. dissolutionThe solid was then dissolved in ethanol (150 ml)
5. customthe reaction hydrogenated on a parr at 40 psi overnight
6. filtrationThe reaction was filtered under nitrogen
7. customthe filtrate was evaporated to dryness