Di-tert-butyl dicarbonate → (4-Hydroxybenzyl)phenethylcarbamic acid tert-butyl ester

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Reaction Steps

Suspend 4-(phenethylaminomethyl)phenol (0.750 g, 3.30 mmol) in dichloromethane (10 mL). Add a solution of (BOC)2O (1.08 g, 4.95 mmol) in dichloromethane (6.5 mL). Quench with 1.0 N NaOH (75 mL) after 19 hours. Extract with dichloromethane (2× 200 mL). Wash the organic layer with brine (1× 75 mL), dry over Na2SO4, filter and concentrate. Purify by flash chromatography, eluting with 20-30% ethyl acetate in hexanes to give the title compound (0.570 g, 52.8%): MS ES+ 328.3 (M+H)+, base peak ES+ 272.1 (M+2H—C(CH3)3)+, ES− 326.3 (M−H)−; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 30-99% over 19 min], tR=14.7 min, 100% purity.

Provenance & Evidence