HCID 59543150, compound → 4-{[Tert-butyl(dimethyl)silyl]oxy}-3-fluorocyclohexanol

HRID 1970986Notes

Reaction equation

HRID 1970986 reaction equation
C([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:11]([F:23])[CH2:10]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[Si:16]([O:15][CH:12]1[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH:11]1[F:23])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

4

Reactant 1

HCID 59543150HCID 59543150, compound

Product 1

HCID 595431354-{[Tert-butyl(dimethyl)silyl]oxy}-3-fluorocyclohexanol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent2×

Procedure

To a stirred solution {[4-(benzyloxy)-2-fluorocyclohexyl]oxy}(tert-butyl)dimethylsilane (4.66 g, 13.8 mmol) in MeOH (30 mL) was added Pd(OH)2 in MeOH (20 mL). The flask was evacuated and filled with hydrogen several times, and left to stir overnight under hydrogen atmosphere. The mixture was diluted with DCM, filtered through a pad of Celite, and concentrated to afford the title compound.

Workup

  1. customThe flask was evacuated
  2. additionfilled with hydrogen several times
  3. waitleft
  4. additionThe mixture was diluted with DCM
  5. filtrationfiltered through a pad of Celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-869aa63bad364d6daf855a00922fe010
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

Loading…