(1R,2S,4R,5S)-5-(tert-Butyldiphenylsilyloxy)bicyclo[2.2.1]heptan-2-ol → HCID 58951272, Verbindung

HRID 46154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46154
[C:1]([Si:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][C@H:7]1[CH2:12][C@H:11]2[CH2:13][C@@H:8]1[CH2:9][C@@H:10]2[OH:14])([CH3:4])([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Si:5]([O:6][C@H:7]1[CH2:12][C@H:11]2[CH2:13][C@@H:8]1[CH2:9][C:10]2=[O:14])([C:1]([CH3:4])([CH3:2])[CH3:3])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 58951248(1R,2S,4R,5S)-5-(tert-Butyldiphenylsilyloxy)bicyclo[2.2.1]heptan-2-olHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 58951272HCID 58951272, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Silica gel 60 (particle size, 0.040-0.063 mm, CAS # 63231-67-4, from EMD Chemical Inc., 21 g) was added to a solution of (1R,2S,4R,5S)-5-(tert butyldiphenylsilyloxy)-bicyclo[2.2.1]heptan-2-ol (6.75 g, 18.4 mmol) in anhydrous dichloromethane (100 mL). The mixture was cooled to 0° C. Pyridinium chlorochromate (6.35 g, 29.5 mmol) was added to the mixture. The reaction mixture was gradually warmed to ambient temperature and stirred at this temperature for 16 h. The mixture was diluted with dichloromethane, and filtered through a pad of silica gel. Removal of the solvents gave the title compound as a colorless viscous oil.

Aufarbeitung

  1. temperatureThe reaction mixture was gradually warmed to ambient temperature
  2. filtrationfiltered through a pad of silica gel
  3. customRemoval of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-c00205bd887e46bab99a16d804fff4aa
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541592B2

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