Acetic Acid → 5-Chloro-2-(4-fluorobenzylamino)-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Participants

Reaction Steps

In methanol (10 ml) were dissolved 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol produced in Example (1) (0.5 g) and 4-fluorobenzaldehyde (0.2 g). To the solution were added acetic acid (0.1 g) and cyano sodium borohydride (0.1 g). The mixture was concentrated, to which were added water (60 ml) and ethyl acetate (50 ml), followed by extraction. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off to leave 5-chloro-2-(4-fluorobenzylamino)-α-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.56 g) as a colorless oily product.

Provenance & Evidence