Hydrogen Peroxide → HCID 59226035, compound

HRID 2370278Notes

Reaction equation

HRID 2370278 reaction equation
B1C2CCCC1CCC2.[C:10]([O:14][C:15](=[O:34])[NH:16][C:17]1([CH2:31][CH:32]=[CH2:33])[CH2:22][CH2:21][CH:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11].[OH-:35].[Na+].OO>C1COCC1>[C:10]([O:14][C:15](=[O:34])[NH:16][C:17]1([CH2:31][CH2:32][CH2:33][OH:35])[CH2:22][CH2:21][CH:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 59226056HCID 59226056, compound

Product 1

HCID 59226035HCID 59226035, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

16.2 mL (8.12 mmol) of a 0.5M solution of 9-BBN in THF were added to a solution of 1.00 g (2.71 mmol) of [1-allyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-carbamic acid tert-butyl ester (31) in 5 mL THF at 0° C. The reaction mixture was allowed to warm to room temperature over night, before being cooled to 0° C. Then, 20 mL of 3M aqueous sodium hydroxide and 20 mL of 30% aqueous hydrogen peroxide were added slowly, and the mixture was stirred for 12 h. The mixture was extracted twice with ethyl acetate, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. 0.85 g of the title compound 32 could be isolated as mixture of diastereoisomers in a purity sufficient for further conversion. Rt=2.03 min, 2.10 min (Method C). Detected mass: 388.3 (M+H+).

Workup

  1. temperaturebefore being cooled to 0° C
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3914bcb7932c4a3d87d35b0a3c7044f5
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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