Hydrogen Peroxide → tert-Butyl 4-(4-carbamoylphenoxy)piperidine-1-carboxylate

HRID 459928Notes

Reaction equation

HRID 459928 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-:24].[K+].[K+].OO>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:24])[NH2:22])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 23019443tert-Butyl 4-(4-cyanophenoxy)piperidine-1-carboxylate

Product 1

HCID 23068080tert-Butyl 4-(4-carbamoylphenoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine 4-(4-cyano-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester Example 9, step 1, 215 mg, 0.71 mmol) and potassium carbonate (49 mg, 0.36 mmol) in DMSO (35 mL) at 0° C. Then add dropwise hydrogen peroxide (213 μL). Then stir at room temperature for 1 h. Quench the reaction with water (10 mL) and extract with EtOAc/hexanes (2/1, 3×20 mL). Combine the organic layers, dry over magnesium sulfate, filter and concentrate to give the title compound.

Workup

  1. customat 0° C
  2. customQuench
  3. customthe reaction with water (10 mL)
  4. extractionextract with EtOAc/hexanes (2/1, 3×20 mL)
  5. dry with materialCombine the organic layers, dry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-b1976db4cf714a209ddbac7c8254e116
Source dataset
uspto-grants-2007_03
Patent number
US07196100B2

Reaction notes

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