3-(((benzyloxy)carbonyl)amino)-N-(2-butoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride → 3-amino-N-(2-butoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride

Participants

Reaction Steps

Under a nitrogen atmosphere, 10% pd/C (100 mg) was added to a solution of 3-(((benzyloxy)carbonyl)amino)-N-(2-butoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride (0.38 g, 0.95 mmol) in 4 mL of methanol. The flask was degassed and placed under a hydrogen atmosphere, stirring for 24 hours at room temperature. The suspension was filtered through a pad of celite washing with methanol, and the filtrate was concentrated under reduced pressure to give 252 mg of clear viscous oil (quantitative yield). 1H NMR (400 MHz, D2O) δ 0.78-0.82 (t, J=7.4 Hz, 3H), 1.08 (s, 6H), 1.22-1.30 (sext, J=7.4 Hz, 6H), 1.45-1.52 (m, 2H), 1.77-1.81 (m, 2H), 3.04 (s, 6H), 3.36-3.40 (m, 2H), 3.45-3.49 (t, J=6.5 Hz, 2H), 3.82-3.83 (br m, 2H); LRMS (ESI/APCI) m/z 231 [M]+.

Provenance & Evidence