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

HRID 1385520Notes

Reaction equation

[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1.[O:12](C(OC(C)(C)C)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O>C1COCC1>[C:16]([O:15][C:13]([NH:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:6]=1)=[O:12])([CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 65 °C

Procedure

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 NMR (CDCl3, 250 MHz) δ7.15 (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) δ157.7, 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)

Workup

temperaturethe reaction mixture was warmed
customThe solvents were removed under reduced pressure, and flash chromatography (SiO2, 4×15 cm, 20% EtOAc/hexane)

Sources & evidence

ORD record: ord-69d7e7d5d49c4e7bb94023bf83ce7ea7
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262271B1

Reaction notes

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