HCID 67117422, compound → HCID 67117411, compound

HRID 1784663Notes

Reaction equation

HRID 1784663 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:13][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][CH2:16][CH:17]=2)=[CH:8][CH:7]=1)(=O)C>[Pd].C(OCC)(=O)C>[OH:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 67117422HCID 67117422, compound

Product 1

HCID 67117411HCID 67117411, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on charcoal was added to the solution of 3-(4-acetoxymethylphenyl)-1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine (0.71 g, 2.1 mmol) in ethyl acetate and stirred under hydrogen atmosphere. After filtration with celite and removal of the solvent under reduced pressure, methanol and 1N aqueous sodium hydroxide were added and stirred. Organic solvents were removed under reduced pressure after addition of water and extracted with ethyl acetate, washed with water and brine and dried over sodium sulfate. Removal of the solvent under reduced pressure and the residue was purified by silica gel chromatography (eluent; hexane/ethyl acetate=3/1) to give 3-(4-hydroxymethylphenyl)-1-(tert-butoxycarbonyl)piperidine (0.39 g, 62%).

Workup

  1. filtrationAfter filtration
  2. customwith celite and removal of the solvent under reduced pressure, methanol and 1N aqueous sodium hydroxide
  3. additionwere added
  4. stirringstirred
  5. customOrganic solvents were removed under reduced pressure
  6. additionafter addition of water
  7. extractionextracted with ethyl acetate
  8. washwashed with water and brine
  9. dry with materialdried over sodium sulfate
  10. customRemoval of the solvent under reduced pressure
  11. customthe residue was purified by silica gel chromatography (eluent; hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-1d3ed45b9ec942bc96557bdad304f18f
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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