Benzylethanolamine → (R)-1-(benzyl(2-hydroxyethyl)amino)propan-2-ol

Participants

Reaction Steps

To a solution of (2S)-2-hydroxypropyl 4-methylbenzenesulfonate (540 g, 2.34 mol) in EtOH (3 L) at 0° C. was added a solution of KOH (160 g, 2.5 mol) in ethanol (2 L). The mixture was maintained at room temperature overnight. Upon completion, 2-benzylamino-ethanol (500 g, 3.3 mol) was added to the reaction, and the resulting mixture was stirred at room temperature for two days. Boc2O (500 g, 2.29 mol) was then added and the mixture was stirred for another day. The mixture was then filtered, the filter cake washed with ethanol (500 mL), and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc (3.5 L), washed with water (500 mL) and brine (500 mL), and concentrated in vacuo. The resulting crude residue was purified by silica gel chromatography (1:2 EtOAc:petroleum ether) to afford the title compound as a brown oil.

Provenance & Evidence