Hydrogen Peroxide → HCID 24894018, compound

HRID 2196111Notes

Reaction equation

HRID 2196111 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:29])[C:7]=1[CH2:8][C:9]([C:11]1[C:26]2[O:25][CH2:24][C:18]3([CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH2:17][O:16][C:15]=2[C:14]([O:27][CH3:28])=[CH:13][CH:12]=1)=[O:10].[OH:30]O>C(Cl)Cl.C[Re](=O)(=O)=O.O=[Mn]=O>[Cl:29][C:6]1[CH:5]=[N+:4]([O-:30])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C:9]([C:11]1[C:26]2[O:25][CH2:24][C:18]3([CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[CH2:17][O:16][C:15]=2[C:14]([O:27][CH3:28])=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 2

HCID 784Hydrogen PeroxideHCID 25005525HCID 25005525, compound

Product 1

HCID 24894018HCID 24894018, compound

Reagents, catalysts & solvents 3

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

Procedure

To a solution 2-(3,5-Dichloropyridin-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),4′-tetrahydropyran]-6-yl}ethanone [127] (66 mg, 150 μmmol) in CH2Cl2 (2 mL) was added 30% H2O2 (45 μL) and methyltrioxorhenium(VII) (10 mg). The mixture was stirred for 18 h, added MnO2 (10 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 5.6 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-11133b768ca5402b88b5a2eea709736e
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

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