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

HRID 46154Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-c00205bd887e46bab99a16d804fff4aa
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541592B2

Reaction notes

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