Acetic Acid → 2-(3,4-Dibenzyloxybenzyl)amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Participants

Reaction Conditions

Reaction Steps

In methanol (20 ml) were dissolved 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.6 g) and 3,4-dibenzyloxybenzaldehyde (0.55 g). To the solution were added acetic acid (0.12 g) and cyano sodium borohydride (0.13 g). The mixture was stirred for 1.5 hour at 60° C. The reaction mixture was concentrated, to which were added water (50 ml) and ethyl acetate (80 ml), followed by extraction. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to leave 2-(3,4-dibenzyloxybenzyl)amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.83 g) as colorless crystals, m.p.: 118-120° C.

Provenance & Evidence