Water → tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

Participants

Reaction Steps

(2-Hydroxy-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester (11.3 g, 0.06 mol) and triethylamine (18.2 g, 0.18 mol) in DMSO (180 mL) at 25° C. was treated with a solution of pyridine-sulfurtrioxide complex (28.6 g, 0.18 mol) in DMSO (150 mL). The resulting mixture was stirred for 0.5 h, poured into H2O (100 mL) and extracted with ether (3×100 mL). The organics were washed with 10% citric acid(aq) (250 mL), saturated NaHCO3 (250 mL) and then with brine (2×250 mL). The organics were dried and concentrated to an off-white solid which was recrystallized from hexanes to afford the desired material (8.0 g, 71%) as white needles: 13C NMR (DMSO-d6, 100 MHz) δ 202.07, 155.58, 78.95, 58.64, 28.42, 21.58.

Provenance & Evidence