Hydrogen Peroxide → HCID 18009116, compound

HRID 987496Notes

Reaction equation

HRID 987496 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:13]2[CH:17]=[CH:16][N:15]=[C:14]2[CH3:18])[CH2:10][CH:11]=[CH2:12])=[CH:5][C:4]=1[F:19])#[N:2].C12BC(CCC1)CCC2.C([O-])(O)=[O:30].[Na+].OO>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([N:13]2[CH:17]=[CH:16][N:15]=[C:14]2[CH3:18])[CH2:10][CH2:11][CH2:12][OH:30])=[CH:5][C:4]=1[F:19])#[N:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 516892Sodium BicarbonateHCID 18009120HCID 18009120, compound

Product 1

HCID 18009116HCID 18009116, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the olefin from Step J (1.303 g, 5.11 mmol) in 10 mL of THF at 0° C. was added a solution of 9-borabicyclo[3.3.1]nonane in THF (50 mL, 25.5 mmol, 0.5 M). After one hour, the reaction was warmed to room temperature for 3 hours, then recooled to 0° C. A solution (20 mL) of sat. aq. NaHCO3 and 30% aq. H2O2 (2:1) was added, and the reaction was warmed to room temperature. After 30 minutes, the mixture was partitioned between CHCl3 and aq. NaHCO3 solution, and the aqueous phase was extracted with CHCl3. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (5-8% MeOH/CH2Cl2, then rechromatographed using 50-100% acetone/CH2Cl2) provided the titled compound as a pale yellow oil.

Workup

  1. customrecooled to 0° C
  2. temperaturethe reaction was warmed to room temperature
  3. waitAfter 30 minutes
  4. customthe mixture was partitioned between CHCl3 and aq. NaHCO3 solution
  5. extractionthe aqueous phase was extracted with CHCl3
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel chromatography (5-8% MeOH/CH2Cl2
  10. customrechromatographed

Sources & evidence

ORD record
ord-f8d9138ab24747f19d9647738698bee3
Source dataset
uspto-grants-2003_10
Patent number
US06632818B2

Reaction notes

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