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

HRID 965222

Reaktionsgleichung

Reaktionsgleichung von HRID 965222
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 67646800(+/-)cis-1-[(4-Phenoxy)phenoxy]-2-tert-butoxycarbonylaminoindaneAusbeute 39,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)KatalysatorHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-33439e50557a459ca508bceeede8dec4
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773463

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