Ethanol → (2-(Benzyloxycarbonylamino)-2-methylpropyl)dimethylsulfonium iodide

Participants

Reaction Steps

To a 15 mL pressure tube was added a solution of benzyl 2-methyl-1-(methylthio)propan-2-ylcarbamate in absolute ethanol (0.5 mL, 6.8 M) (1.00 g, 3.9 mmol) and methyl iodide (1.23 mL, 5 equiv, 19.7 mmol). The reaction mixture was covered with aluminum foil and left to stir for 3 days. The light yellow suspension was filtered and washed with diethyl ether (20 mL). The mother liquor was concentrated to a deep yellow solid. This solid was recrystallized from isopropyl alcohol and diethyl ether and combined with the first crop of product 1.29 g (83.6%). 1H NMR (D2O, 400 MHz): δ 1.41 (s, 6H), 2.51 (s, 2H), 2.98 (s, 2 H). LRMS (ESI−) for C14H22NO2S+ (268.1); Found: 268 (M+).

Provenance & Evidence