Sodium Acetate → 850991-46-7

HRID 749116Notes

Reaction equation

HRID 749116 reaction equation
[OH:1][CH:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][N:7]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][CH2:3]1.C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.CCOCC>[O:1]=[C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][N:7]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 57485771HCID 57485771, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 57485772850991-46-7Yield 97.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl 4-hydroxy-6-azabicyclo[3.2.1]octane-6-carboxylate (800 mg, 3.52 mmol) in dry dichloromethane (75 ml) was added Celite (2 g), sodium acetate (0.82 g, 10 mmol) and pyridinium chlorochromate (1.1 g, 5.1 mmol). The mixture was stirred under nitrogen for 66 h. The dark suspension was diluted with ether (50 ml) and filtered through a plug of silica gel to give a light brown solution. Removal of solvent by rotary evaporation and purification by column chromatography of the residue, using a methanol/dichloromethane gradient (0-10% methanol) as eluent, gave the ketone as a pale yellow oil (770 mg, 96%).

Workup

  1. filtrationfiltered through a plug of silica gel
  2. customto give a light brown solution
  3. customRemoval of solvent
  4. customby rotary evaporation and purification by column chromatography of the residue

Sources & evidence

ORD record
ord-c1ad495e951d4e4f9efd6bf7467e87bd
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Reaction notes

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