4-Phenoxyphenol → (+/-)cis-1-[(4-Phenoxy)phenoxy]-2-tert-butoxycarbonylaminoindane

HRID 965222Notes

Reaction equation

HRID 965222 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].[O:18]([C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[O:18]([C:25]1[CH:26]=[CH:27][C:28]([O:31][C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C@@H:10]2[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 132544-PhenoxyphenolHCID 53697243(+/-)N-tert-butoxycarbonyl-1,2-iminoindane

Product 1

HCID 67646800(+/-)cis-1-[(4-Phenoxy)phenoxy]-2-tert-butoxycarbonylaminoindaneYield 39.8%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6212ChloroformSolvent2×

Procedure

The title compound was prepared in a similar manner to Preparation 18 from (±) N-tert-butoxycarbonyl-1,2-iminoindane (3 g, 13 mmol), 4-phenoxyphenol (2.42 g, 13 mmol), pyridinium p-toluenesulfonate (50 mg) and chloroform (100 ml). After a reaction time of 3 h, the reaction was diluted with chloroform (100 ml) then washed sequentially with saturated aq. sodium bicarbonate, water and brine. After drying over Na2 SO4, volatiles were removed in vacuo and the residue subjected to column chromatography on neutral alumina eluting with 10% diethyl ether in hexanes to afford the title compound (2.16 g) as a foam.

Workup

  1. washthen washed sequentially with saturated aq. sodium bicarbonate, water and brine
  2. customAfter drying over Na2 SO4, volatiles
  3. customwere removed in vacuo

Sources & evidence

ORD record
ord-33439e50557a459ca508bceeede8dec4
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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