Monobenzone → (+/-)cis-1-(4Benzyloxyphenoxy)-2-tert-butoxycarbonylaminoindane

HRID 965220

Reaktionsgleichung

Reaktionsgleichung von HRID 965220
[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]([O:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=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]([O:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][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:30][CH:31]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

5

Versuchsvorschrift

The title compound was prepared in a similar manner to Preparation 18 from (±) N-tert-butoxycarbonyl-1,2-iminoindane (5 g, 21.6 mmol), 4-benzyloxyphenol (4.3 g, 21.6 mmol), pyridinium p-toluenesulfonate (100 mg) and chloroform (150 ml). After a reaction time of 3 h, the reaction was diluted with chloroform (100 ml) then washed sequentially with water and brine. After drying over sodium sulfate, volatiles were removed in vacuo and the residue subjected to column chromatography on silica gel eluting with 10% diethyl ether in hexanes to afford a light brown solid which was recrystallised to afford the title compound (3.6 g) as a white solid. (from diethyl etherhexanes).

Aufarbeitung

  1. washthen washed sequentially with water and brine
  2. dry with materialAfter drying over sodium sulfate, volatiles
  3. customwere removed in vacuo
  4. customto afford a light brown solid which
  5. customwas recrystallised

Quellen und Nachweise

ORD-Eintrag
ord-4ecfdc61d0c14b608e9264b12abd4656
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773463

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