Acetic Acid → N-Benzyloxycarbonyl-2-amino-2-[4-propoxybenzyl]-ethanol

Participants

Reaction Steps

4.15 g (11.2 mmol) of N-benzyloxycarbonyl-3-[4-propoxyphenyl]-alanine-methyl ester is dissolved in 20 ml of tert-butyl methyl ether and mixed with 0.17 g (4.5 mmol) of sodium borohydride. At 0° C., 6 ml of methanol is added and it is stirred for three hours under argon at a temperature below 5° C. Then, 0.8 ml of acetic acid, dissolved in 3 ml of tetrahydrofuran, is added, mixed with 3 ml of water and stirred for ten minutes at room temperature. The organic phase is separated, washed with water and dried on sodium sulfate. The drying agent is suctioned off, the filtrate is concentrated by evaporation and the residue is chromatographed for purification on silica gel (eluent: ethyl acetate/hexane).

Provenance & Evidence