Hydrogen Peroxide → 1-Ethyl-4-[2-fluoro-3-(methylsulfonyl)phenyl]-1,2,3,6-tetrahydropyridine

HRID 2358151Notes

Reaction equation

HRID 2358151 reaction equation
[CH2:1]([N:3]1[CH2:8][CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11](SC)[C:10]=2[F:17])[CH2:5][CH2:4]1)[CH3:2].[S:18](=[O:22])(=O)(O)[OH:19].OO.[C:25](OCC)(=O)C.CO>[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH2:1]([N:3]1[CH2:4][CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([S:18]([CH3:25])(=[O:22])=[O:19])[C:10]=2[F:17])[CH2:7][CH2:8]1)[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 21584119Ethylacetate methanolHCID 589884171-Ethyl-4-(2-fluoro-3-(methylthio)phenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 166553451-Ethyl-4-[2-fluoro-3-(methylsulfonyl)phenyl]-1,2,3,6-tetrahydropyridine

Reagents, catalysts & solvents 1

HCID 26052Sodium tungstateCatalyst

Procedure

Preparation according to preparation 64: 1-ethyl-4-[2-fluoro-3-(methylthio)phenyl]-1,2,3,6-tetrahydropyridine (22.5 g, 89.6 mmol), sulfuric acid (1 M, 180 ml), sodium tungstate (0.296 g, 0.89 mmol), hydrogen peroxide (30%, 22.9 ml, 224 mmol). Flash column chromatography (ethyl acetate/methanol, 1:1) gave the title compound (17.2 g). MS m/z (rel. intensity, 70 eV) 283 (M+, 63), 268 (bp), 146 (51), 110 (87), 56 (59).

Workup

  1. customPreparation
  2. customaccording to preparation 64

Sources & evidence

ORD record
ord-f96df6e4d0f84c4fae68993aed822df6
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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