Acetic Acid → 5-Chloro-2-(furan-2-ylmethyl)amino-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Participants

Reaction Conditions

Reaction Steps

In methanol (15 ml) were dissolved 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.5 g) produced in Example (1) and furfural (0.15 g). To the solution were added acetic acid (0.1 g) and cyano sodium borohydride (0.11 g). The mixture was stirred for 40 minutes at 60° C. The reaction mixture was concentrated, to which were added water (30 ml) and ethyl acetate (50 ml), followed by subjecting the mixture to extraction. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give 5-chloro-2-(furan-2-ylmethyl)amino-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.6 g) as a colorless oily product.

Provenance & Evidence