m-Chloroperbenzoic acid → tert-Butyl N-(2-oxiranylmethyl)carbamate

Participants

Reaction Steps

To a solution of 28.9 g (184 mmol) of tert-butyl allylcarbamate in 400 mL of dichloromethane was added 103 g (460 mmol) of 77% 3-chloroperoxybenzoic acid at room temperature. The reaction mixture was stirred at room temperature overnight. The solid was filtered and the filtrate was concentrated. The residue was taken up in diethyl ether and washed with 5% sodium hydrosulfite (3×), saturated sodium bicarbonate (3×), brine (3×), and dried over anhydrous magnesium sulfate. Removal of solvent gave 21 g (66%) of tert-butyl 2-oxiranylmethylcarbamate as a liquid. 1H-NMR (400 MHz, CDCl3): δ 4.73 (br s, 1H), 3.53 (br s, 1H), 3.21 (m, 1H), 3.08 (br s, 1H), 2.77 (t, J=4 Hz, 1H), 2.58 (m, 1H), 1.43 (s, 9H).

Provenance & Evidence