HCID 57788451, compound → HCID 57788459, compound

HRID 215734Notes

Reaction equation

HRID 215734 reaction equation
C(OC[O:10][CH2:11][C@@H:12]([CH3:27])[CH2:13][CH2:14][CH2:15][C:16]([CH3:26])([CH3:25])[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[Si:18]([O:17][C:16]([CH3:25])([CH3:26])[CH2:15][CH2:14][CH2:13][C@H:12]([CH3:27])[CH2:11][OH:10])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 57788451HCID 57788451, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57788459HCID 57788459, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

Removal of BOM-protecting group in compound 3. (s)-6-(tert-Butyldimethylsilyloxy)-2,6-dimethyl-heptan-1-ol (4). 1st procedure. To a solution of compound 3 (1.5 g, 3.8 mmol) in ethyl acetate (10 mL) was added Pd/C (10%, 100 mg) at room temperature. The reaction mixture was stirred for 6 days under a continuous stream of hydrogen (from balloon) and Pd/C (100 mg in portions) was added 3 times per day. Then, the mixture was filtered and the solvent was evaporated under reduced pressure. The oily residue was chromatographed on silica gel using hexane/AcOEt (9:1) as an eluent yielding an oily alcohol 4 (0.80 g, 77%).

Workup

  1. customRemoval of BOM-protecting group in compound 3
  2. additionwas added 3 times per day
  3. filtrationThen, the mixture was filtered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe oily residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-f6c02834cf3c4c08a5bd41443096ca2e
Source dataset
uspto-grants-2012_06
Patent number
US08193171B2

Reaction notes

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