Hydrogen Peroxide → HCID 59556045, compound

HRID 1809848Notes

Reaction equation

HRID 1809848 reaction equation
[CH2:1]([C:4]1([OH:27])[C@@H:8]([NH:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:7][N:6]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:5]1)[CH:2]=[CH2:3].B1C2CCCC1CCC2.OO.CC([O-])=[O:41].[Na+].O>C1COCC1.O>[CH2:13]([O:12][C:10]([NH:9][C@H:8]1[CH2:7][N:6]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:5][C:4]1([OH:27])[CH2:1][CH2:2][CH2:3][OH:41])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 23681166Acetic acid, sodium salt, monohydrateHCID 59556099HCID 59556099, compound

Product 1

HCID 59556045HCID 59556045, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.85 g of allyl alcohol of step C in 20 mL of anhydrous THF was added a solution of 15 mL of 0.5 N 9-BBN. The reaction was stirred for 2 days. Water (0.5 mL) was added followed with 1 mL of 30% H2O2 and 1 mL of NaOAc/water. After being stirred for 1 h, the organic phase was separated. The water solution was neutralized with HCl and extracted with EtOAc twice. The combined organic phase was dried over Na2SO4. Solvent was removed under vacuum. Column chromatography on silica gel using pure EtOAc as eluent provided 0.80 g of the title compound. MS (M+H)+395.

Workup

  1. stirringAfter being stirred for 1 h
  2. customthe organic phase was separated
  3. extractionextracted with EtOAc twice
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-567a53874e0d4461af07c543f31909a7
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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