24424-99-5

39895-56-2

123986-64-1

GENERAL STEPS: A mixture of 4-(aminomethyl)benzenemethanol (1 g, 7.29 mmol) and di-tert-butyl dicarbonate (1.59 g, 7.29 mmol) in dichloromethane (30 mL) was reacted at room temperature with stirring overnight. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with the eluent being a solvent mixture of dichloromethane and ethyl acetate (1:1, v/v) to afford tert-butyl 4-(hydroxymethyl)benzylcarbamate (0.8 g, 2.28 mmol, 31% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.37 (s, 1H), 7.22 (dd, J = 27.8, 8.0 Hz, 4H), 5.13 (t, J = 5.7 Hz, 1H), 4.46 (d, J = 5.7 Hz, 2H), 4.10 (d, J = 6.1 Hz, 2H), 1.36 (s, 9H ).