m-Chloroperbenzoic acid → tert-Butyl 2-pyridylmethylcarbamate N-oxide

HRID 748283Notes

Reaction equation

HRID 748283 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].ClC1C=CC=C(C(OO)=[O:24])C=1>C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH+:8]([O-:24])[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12069550N-Boc-2-aminomethylpyridine

Product 1

HCID 86596464tert-Butyl 2-pyridylmethylcarbamate N-oxideYield 91.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-pyridylmethylcarbamate (11.4 g, 54 mmol) and 3-chloroperbenzoic acid (77%, 5.9 g, 71 mmol) were dissolved in ethyl acetate (150 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 (1:5, v/v) were collected and concentrated to give the titled compound (11.1 g, 90%).

Workup

  1. customThe solvent was evaporated
  2. washThe fractions eluted with methanol-ethyl acetate (1:5
  3. customv/v) were collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2de882b35ceb4ca58d171630aa277557
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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