Vanillylamine → HCID 15713917, compound

Participants

Reaction Steps

To a solution of 4-hydroxy-3-methoxybenzylamine (1.0 g, 5.27 mmol) in acetonitrile (30 mL) was added tert-butyldicarbonate (1.27 g, 5.80 mmol) and di-isopropylethylamine (1.84 mL, 10.54 mmol). The reaction was stirred at room temperature for 16 h before being partitioned between EtOAc (60 mL) and water (30 mL). The aqueous phase was separated and re-extracted with EtOAc (3×25 mL) and the combined organic extracts were washed with brine (60 mL), dried over MgSO4, filtered and concentrated. Purification by flash chromatography (40% EtOAc/hexanes) gave tert-Butyl(4-hydroxy-3-methoxybenzyl)carbamate. LCMS 275.9 (M+1)+.

Provenance & Evidence