Benzyl Alcohol → Benzyl [1-(3-methoxyphenyl)-1-methylethyl]carbamate

Participants

Reaction Conditions

Reaction Steps

Into a round bottom flask, 2-(3-methoxy-phenyl)-2-methyl-propionic acid (15.00 g, 77.23 mmol), toluene (150.0 mL, 1408 mmol) and triethylamine (10.2 mL, 73.4 mmol) were added a room temperature under an atmosphere of Nitrogen. Diphenylphosphonic azide (15.8 mL, 73.4 mmol) was added. The reaction was heated at 85° C. for 3 hours. benzyl alcohol (7.99 mL, 77.2 mmol) and triethylamine (10.2 mL, 73.4 mmol) was added. The reaction was heated to reflux overnight under an atmosphere of Nitrogen. 10% Citric acid (300 mL) was added to the reaction mixture at room temperature. The reaction was extracted with EtOAc (3×250 mL). The combined organic was washed with brine, and dried over magnesium sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum. The product was isolate via ISCO column chromatography with hexane and EtOAc as eluant (15% EtOAc) to give [1-(3-Methoxy-phenyl)-1-methyl-ethyl]-carbamic acid benzyl ester (21.30 g, 92%). 1H-NMR (DMSO-D6, 400 MHz): δ 7.68 (bs, 1H), 7.25-7.42 (m, 5H), 7.20 (t, 1H), 6.91 (d, 1H), 6.86 (s, 1H), 6.75 (d, 1H), 4.94 (s, 2H), 3.70 (s, 3H), 1.51 (s, 6H).

Provenance & Evidence