Hydrogen Peroxide → HCID 58794441, compound

HRID 459921Notes

Reaction equation

HRID 459921 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][N: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[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:24])[NH2:22])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 57027834tert-Butyl 4-(5-cyanopyridin-2-yloxy)piperidine-1-carboxylate

Product 1

HCID 58794441HCID 58794441, compoundYield 193.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

Combine a solution of 4-(5-cyano-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (1630 mg, 5.38 mmol) in DMSO (50 mL) with potassium carbonate (371 mg, 2.69 mmol). Cool the solution to 0° C. and add slowly hydrogen peroxide (1.61 mL). After 10 min, stir the reaction mixture at room temperature for 2 h. Add water (25 mL) and extract twice with CH2Cl2 (30 mL). Dry the organic layer over sodium sulfate, filter and concentrate to provide the title compound (1669 mg, 97%) as a white solid.

Workup

  1. extractionAdd water (25 mL) and extract twice with CH2Cl2 (30 mL)
  2. dry with materialDry the organic layer over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-9a3817468706461c8abf9d142b1cdeca
Source dataset
uspto-grants-2007_03
Patent number
US07196100B2

Reaction notes

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