4-Hydroxybiphenyl → (+/-)cis-1-(4-Phenylphenoxy)-2-tert-butoxycarbonylaminoindane

HRID 965229

Reaction equation

HRID 965229 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:10]2[CH2:11][C:12]3[C:17]([CH:9]12)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]1([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[C:18]1([C:24]2[CH:25]=[CH:26][C:27]([O:30][C@@H:9]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH2:11][C@@H:10]3[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:28][CH:29]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 71034-HydroxybiphenylHCID 53697243(+/-)N-tert-butoxycarbonyl-1,2-iminoindane

Product 1

HCID 18661298(+/-)cis-1-(4-Phenylphenoxy)-2-tert-butoxycarbonylaminoindaneYield 33.4%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6212ChloroformSolvent

Procedure

A solution of (±) N-tert-butoxycarbonyl-1,2-iminoindane (5 g, 22 mmol), 4-phenylphenol (3.73 g, 22 mmol) and pyridinium p-toluenesulfonate (108 mg) in chloroform (150 ml) was heated at reflux for 2 h. On cooling, the solution was washed sequentially with 10% aq. NaOH, water and then brine. After drying over MgSO4, solvents were removed in vacuo and the resultant brown oil subjected to column chromatography on silica gel eluting with 20% diethyl ether in hexanes to afford the title compound (2.95 g).

Workup

  1. temperatureat reflux for 2 h
  2. temperatureOn cooling
  3. washthe solution was washed sequentially with 10% aq. NaOH, water
  4. dry with materialAfter drying over MgSO4, solvents
  5. customwere removed in vacuo

Sources & evidence

ORD record
ord-629176bc4bda49a793cbe83bed9ddf43
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Linked notes

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