Hexane → tert-butyl 7-(benzyloxy)-9H-carbazol-2-ylcarbamate

HRID 1879531Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:17][CH:16]=2)=[C:11]([N+:29]([O-])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC>P(OCC)(OCC)OCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:17][C:16]=3[NH:29]2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 145 °C

Procedure

A suspension of tert-butyl 4′-(benzyloxy)-2′-nitrobiphenyl-4-ylcarbamate (740 mg, 1.67 mmol) in 2 mL of triethyl phosphite was heated at 145° C. for 15 h under Ar atmosphere and cooled to rt. It was added 10 mL of hexane and let sit for 10 min. Solid was collected via filtration and washed with ether/hexane (v:v 1/1, 10 mL) and dried under high vacuum to afford tert-butyl 7-(benzyloxy)-9H-carbazol-2-ylcarbamate as a off-white solid (480 mg, 74%). 1H NMR (400 MHz, CDCl3) δ 7.89 (s, 1H), 7.83-7.78 (m, 3H), 7.46 (d, J=7.2 Hz, 2H), 7.38 (m, 2H), 7.32 (d, J=7.2 Hz, 1H), 6.94 (d, J=2.0 Hz, 1H), 6.88 (dd, J=8.8, 2.4 Hz, 1H), 6.83 (dd, J=8.4, 2.0 Hz, 1H), 6.60 (s, 1H), 5.15 (s, 2H), 1.52 (s, 9H); MS (ESI) m/z 389 (M+H+).

Workup

temperaturecooled to rt
filtrationSolid was collected via filtration
washwashed with ether/hexane (v:v 1/1, 10 mL)
customdried under high vacuum

Sources & evidence

ORD record: ord-9410b8b9c96540c7b7c4f5005b7cf200
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318132B2

Reaction notes

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