Benzyl 4-(dimethylamino)-2-methylbutan-2-ylcarbamate → 3-(((benzyloxy)carbonyl)amino)-N-(2-butoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride

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Reaction Conditions

Reaction Steps

A mixture of benzyl(4-(dimethylamino)-2-methylbutan-2-yl)carbamate (500 mg, 1.9 mmol, preparation described in previous experiment) and 2-(chloroethyl)-n-butyl ether (517 mg, 3.8 mmol) was stirred overnight at 75° C. An additional portion of 2-(chloroethyl)-n-butyl ether (517 mg, 3.8 mmol) was added and the mixture stirred for 24 hours at 80° C. The resultant white precipitate was collected on a glass fritted filter and washed with ether to give 388 mg of a white solid (51%). 1H NMR (400 MHz, MeOD) δ 0.86-0.89 (t, J=7.4 Hz, 3H), 1.23 (s, 6H), 1.27-1.33 (sext, J=7.5 Hz, 2H), 1.45-1.50 (m, 2H), 2.05-2.09 (m, 2H), 3.03 (s, 6H), 3.29-3.34 (m, 2H), 3.39-3.34 (t, J=Hz, 2H), 3.48-3.50 (br m, 2H), 3.74 (br s, 2H), 4.99 (s, 2H), 7.17 (s, 1H), 7.31-7.36 (m, 5H). LRMS (ESI/APCI) m/z 365 [M]+.

Provenance & Evidence