Hydrogen Peroxide → HCID 22636329, compound

HRID 2416006Notes

Reaction equation

HRID 2416006 reaction equation
C12BC(CCC1)CCC2.[F:10][C:11]([F:33])([F:32])[CH2:12][NH:13][C:14]([C:16]1([CH2:29][CH:30]=[CH2:31])[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:15].[OH-:34].[Na+].OO>C1COCC1.O>[F:10][C:11]([F:32])([F:33])[CH2:12][NH:13][C:14]([C:16]1([CH2:29][CH2:30][CH2:31][OH:34])[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:15]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 22636303HCID 22636303, compound

Product 1

HCID 22636329HCID 22636329, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

12 ml of 9-borabicyclo[3.3.1]nonane are added dropwise to a solution of 1.5 g (4.52 mmol) of 9-allyl-9H-fluorene-9-carboxylic acid-(2,2,2-trifluoro-ethyl)-amide in 40 ml of THF under nitrogen. Then the mixture is stirred for three hours at ambient temperature. 6 ml of 1M sodium hydroxide solution and 4 ml of 33% hydrogen peroxide solution are then added successively and the resulting mixture is stirred for one hour. The reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is dried over sodium sulphate. The product is purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=1:1).

Workup

  1. stirringthe resulting mixture is stirred for one hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customThe product is purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0fdf92167c544d2180105685574324cf
Source dataset
uspto-grants-2004_11
Patent number
US06821967B2

Reaction notes

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