tert-Butanol → tert-Butyl (6-methylpyridin-3-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-methylnicotinic acid (4.5 g, 32.8 mmol) in toluene (45.0 mL) were added DIPEA (4.67 g, 6.3 mL, 36.1 mmol) and diphenyl phosphorazidate (9.93 g, 7.78 mL, 36.1 mmol) and the suspension was stirred at room temperature for 15 minutes before tert-butanol (24.3 g, 30.8 mL, 328 mmol) was added and the reaction mixture was heated to 80° C. overnight. The reaction mixture was poured on saturated aqueous NH4Cl solution and EtOAc and the layers were separated. The aqueous layer was extracted six times with EtOAc. The organic layers were dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 120 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (5.05 g; 73%). MS (ESI): m/z=209.1 [M+H]+.

Provenance & Evidence