4-Benzylphenol → cis-1-(4-Benzylphenoxy)-2-tert-butoxycarbonylaminoindane

HRID 965224

Reaktionsgleichung

Reaktionsgleichung von HRID 965224
[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].[CH2:18]([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>[CH2:18]([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 75634-BenzylphenolHCID 53697243(+/-)N-tert-butoxycarbonyl-1,2-iminoindane

Produkt 1

HCID 18661294cis-1-(4-Benzylphenoxy)-2-tert-butoxycarbonylaminoindaneAusbeute 38,7 %

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 (2 g, 8.7 mmol), 4-benzylphenol (1.59 g, 8.7 mmol), pyridinium p-toluenesulfonate (30 mg) and chloroform (50 ml). After a reaction time of 3 h, the reaction was diluted with chloroform (50 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 (1.4 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-9646a20809e8443b91dcc89031ac23c6
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773463

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