Acetic Acid → 2-Benzylamino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Participants

Reaction Steps

To a solution of 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.7 g) in methanol (7 ml) were added benzaldehyde (229 mg) and acetic acid (130 mg). The mixture was stirred for 10 minutes at room temperature, to which was added sodium cyano-borohydride (135 mg). The mixture was stirred for 30 minutes at room temperature, to which was added ethyl acetate ester (50 ml). The mixture was washed with water and dried over anhydrous MgSO4, followed by distilling off the solvent. The residue was purified by means of a silica gel column chromatography to give the object 2-benzylamino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.91 g) as a colorless oily compound.

Provenance & Evidence