2-Methylpropylenediamine → 1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Participants

Reaction Steps

Di-t-butyl carbonate (15.7 g.) was added to a solution of (+-(S)-2-amino-1-propanol (5.0 g.) in water (13.2 ml.) and t-butanol (6.6 ml.) at ambient temperature, and the mixture was stirred for 16 hr. at ambient temperature, 1,1-Dimethylethylenediamine (2 ml.) was added and the mixture was stirred at ambient temperature for 1 hr. The solution was poured into water (200 ml.) and extracted with diethyl ether (3×100 ml.). The ethereal extract was washed successively with 1 M-hydrochloric acid (50 ml.), saturated sodium carbonate solution (50 ml.) and brine (100 ml.), and then dried (MgSO4). The solvent was evaporated to give (S)-2-t-butoxycarbonylamino-1-propanol, m.p. 42°-3°.

Provenance & Evidence