Hydrogen Peroxide → 2-(3,5-Dichloro-1-oxido-pyridin-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),3'-oxetane]-6-yl}ethanone

HRID 2196107

Reaction equation

HRID 2196107 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[CH2:8][C:9]([C:11]1[C:24]2[O:23][CH2:22][C:18]3([CH2:21][O:20][CH2:19]3)[CH2:17][O:16][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10].[OH:28]O>C(Cl)Cl.C[Re](=O)(=O)=O.O=[Mn]=O>[Cl:27][C:6]1[CH:5]=[N+:4]([O-:28])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C:9]([C:11]1[C:24]2[O:23][CH2:22][C:18]3([CH2:21][O:20][CH2:19]3)[CH2:17][O:16][C:15]=2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 2

HCID 784Hydrogen PeroxideHCID 250051682-(3,5-Dichloropyridin-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),3'-oxetane]-6-yl}ethanone

Product 1

HCID 250051692-(3,5-Dichloro-1-oxido-pyridin-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),3'-oxetane]-6-yl}ethanone

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(3,5-Dichloropyridin-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),3′-oxetane]-6-yl}ethanone [121] (20.5 mg, 50 μmol) in CH2Cl2 (1 mL) was added 30% H2O2 (15 μL) and methyltrioxorhenium(VII) (5 mg). The mixture was stirred for 18 h, added MnO2 (5 mg) and was stirred for another hour. CH2Cl2 (10 mL) was added and the organic phase was washed with water. The combined organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure. Standard HPLC purification afforded 14 mg of the product.

Workup

  1. stirringwas stirred for another hour
  2. washthe organic phase was washed with water
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. customevaporated to dryness under reduced pressure
  5. customStandard HPLC purification

Sources & evidence

ORD record
ord-0eb6c5e22bcb453e93177ccfb4df0523
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Linked notes

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