Acetic Acid → HCID 21073106, compound

Participants

Reaction Steps

A mixture of tert-butyl[3-(2-amino-5-chlorophenoxy)benzyl]carbamate (3.48 g, 10 mmols), 4-tert-butyldimethylsilyloxybenzaldehyde (2.19 g, 12 mmols), acetic acid (1 ml) and methanol (40 ml) was stirred at room temperature for 1 hour, to which was added sodium cyanoborohydride (0.75 g, 12 mmols). Next, this was stirred at room temperature for 3 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with water, then dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography to give an oil of tert-butyl[3-[2-(4-tert-butyldimethylsilyloxybenzylamino)-5-chlorophenoxy]benzyl]carbamate (2.40 g, 42.4%).

Provenance & Evidence