Acetic Acid → 2-(4-Benzyloxybenzylamino)-alpha-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxybenzyl alcohol

Participants

Reaction Conditions

Reaction Steps

NMR(CDCl3) δ: 1.02(6H,d,J=6.6 Hz), 1.449(9H,s), 2.05(1H,m), 3.64(2H,d,J=6.6 Hz), 4.31(2H,d,J=5.6 Hz), 4.85(1H,m), 6.797(1H,s), 6.6-7.5(7H,m) (5) In methanol (12 ml) were dissolved 2-amino-α-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxybenzyl alcohol (0.36 g), 4-benzyloxy-benzaldehyde (0.2 g) and acetic acid (0.05 g). To the solution was added cyano sodium borohydride (0.065 g). The mixture was stirred for 20 minutes at 60° C. To the reaction mixture was added water (6 ml), which was subjected to extraction with ethyl acetate (60 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to leave 2-(4-benzyloxybenzylamino)-α-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxybenzyl alcohol as a yellow oily product (0.45 g).

Provenance & Evidence