tert-Butyl carbamate → (2-Cyclohexylphenyl)-carbamic acid tert-butyl ester

HRID 1163384Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[C:14](=[O:21])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[NH2:15]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:17]([O:16][C:14](=[O:21])[NH:15][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-bromo-2-cyclohexyl-benzene (5 mmol) in dioxane (20 mL) was added solid Pd(OAc)2 (0.1 g) and solid CsCO3 (10 mmol). tert-Butyl carbamate (7 mmol) was added to the reaction mixture, and the contents were heated at 80° C. for 2 h. The reaction mixture was cooled to room temperature and filtered through Celite. The solvent was removed in vacuo and the residue obtained was purified by flash column chromatography using DCM as eluant to yield (2-cyclohexylphenyl)-carbamic acid tert-butyl ester.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through Celite
customThe solvent was removed in vacuo
customthe residue obtained
customwas purified by flash column chromatography

Sources & evidence

ORD record: ord-c95baa0a6cfb442ba34211686bcffc02
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820821B2

Reaction notes

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