((1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-yloxy)(tert-butyl)diphenylsilane → (1R,2S,4R,5S)-5-(tert-Butyldiphenylsilyloxy)bicyclo[2.2.1]heptan-2-ol

HRID 46153Notes

Reaction equation

HRID 46153 reaction equation
C([O:8][C@H:9]1[CH2:14][C@H:13]2[CH2:15][C@@H:10]1[CH2:11][C@@H:12]2[O:16][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[Si:17]([O:16][C@H:12]1[CH2:11][C@H:10]2[CH2:15][C@@H:13]1[CH2:14][C@@H:9]2[OH:8])([C:30]([CH3:33])([CH3:31])[CH3:32])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 58951349((1R,2S,4R,5S)-5-(Benzyloxy)bicyclo[2.2.1]heptan-2-yloxy)(tert-butyl)diphenylsilaneHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium (10 wt. % on activated carbon, 1.50 g) was added to a solution of ((1R,2S,4R,5S)-5-(benzyloxy)bicyclo[2.2.1]heptan-2-yloxy)(tert-butyl)diphenylsilane (8.47 g, 18.5 mmol) in methanol (50 mL). The mixture was placed under a balloon of hydrogen. After stirring at ambient temperature for 24 h, the mixture was filtered through a pad of Celite. Solvents were removed in vacuo to give the title compound as a colorless viscous oil.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-8d0e5da389194af780dad66de540d60e
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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