Di-tert-butyl dicarbonate → 1,1-Dimethylethyl N-[3-(methoxymethoxy)phenyl]carbamate

Participants

Reaction Conditions

Reaction Steps

A solution of crude 12 (4.13 g, 27 mmol) in 135 mL anhydrous THF was treated with BOC2O (12.14 g, 54 mmol) and the reaction mixture was warmed at reflux (65° C.) for 18 h. The solvents were removed under reduced pressure, and flash chromatography (SiO2, 4×15 cm, 20% EtOAc/hexane) provided pure 13 (6.83 g, 100%) as a yellow oil: 1H NM (CDCl3, 250 MHz) δ 7.15 (m, 2H), 6.94 (m, 1H), 6.68 (m, 1H), 6.58 (br s, 1H), 5.13 (s, 2H), 3.44 (s, 3H), 1.50 (s, 9H); 13C NMR (CDCl3, 62.5 MHz) δ 157.7, 152.5, 139.5, 129.6, 111.9, 110.7, 106.6, 94.2, 80.5, 55.9, 28.2; IR (film) νmax 3337, 2977, 1728, 1605, 1537, 1236, 1153, 1015 cm−1; FABHRMS (NBA/NaI) m/z 276.1203 (C13H19NO4+Na+ requires 276.1212)

Provenance & Evidence