4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid → tert-Butyl [4-(hydroxymethyl)benzyl]carbamate

Participants

Reaction Steps

To 100 ml (100 mM) of 1M borane-THF complex was added 25.13 g (100 mM) of 4-[N-(tert-butoxycarbonyl)aminomethyl]benzoic acid at 0° C. and the mixture was stirred at room temperature for 1.5 hours. The reaction was stopped by adding iced water and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4. The solvent was then distilled off under reduced pressure and the resulting crystal crop was harvested by filtration and rinsed with hexane to provide the title compound as white crystals.

Provenance & Evidence