Tert-Butylamine → Carbamate

Participants

Reaction Steps

To a cooled solution of triphosgene (76 g, 0.256 mol, 0.75 eq.) in dry DCM (150 mL) was added, dropwise at 0° C. over a period of 3 hrs under a N2 atmosphere, a mixture of tert-butylamine (25 g, 0.3418 mol, 1.0 eq.), DMAP (2.08 g, 0.017 mol, 0.05 eq.) and triethylamine (67.1 g, 0.6836 mol, 2.0 eq.) in dry DCM (100 mL). After addition of the mixture was complete, the reaction mixture was stirred at RT for 12 hrs. The reaction mixture was cooled to 0° C. and 2-bromoethanol (106.8 g, 0.854 mol, 2.5 eq.) was added. The reaction mixture was then stirred at RT for 6 hrs, before being diluted with water and extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and then concentrated under reduced pressure. The resulting residue was distilled under reduced pressure to yield carbamate the sub-title compound as a colourless liquid. Yield: 28 g.

Provenance & Evidence