m-Chloroperbenzoic acid → tert-Butyl 2-(2-pyridyl)ethylcarbamate N-oxide

HRID 499482Notes

Reaction equation

HRID 499482 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].ClC1C=CC=C(C(OO)=[O:25])C=1>C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH+:9]([O-:25])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22027815tert-Butyl [2-(pyridin-2-yl)ethyl]carbamate

Product 1

HCID 86628981tert-Butyl 2-(2-pyridyl)ethylcarbamate N-oxideYield 99.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-(2-pyridyl)ethylcarbamate (18.5 g, 83 mmol) and 3-chloroperbenzoic acid (77%, 24.5 g, 109 mmol) were dissolved in ethyl acetate (200 ml), and the mixture was stirred at room temperature for 15 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with methanol-ethyl acetate (1:4, v/v) were collected and concentrated to give the titled compound (19.6 g, 99%).

Workup

  1. customThe solvent was evaporated
  2. washThe fractions eluted with methanol-ethyl acetate (1:4, v/v)
  3. customwere collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-976882f206d147e8b74598cb218c8e7b
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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