Hydrogen Peroxide → HCID 86664657, compound

HRID 1917420Notes

Reaction equation

HRID 1917420 reaction equation
[C:1]([O:5][C:6]([C@@:8]12[CH2:14][C:13](=[CH2:15])[C@@H:12]1[CH2:11][N:10]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:9]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C12BC(CCC1)CCC2.[OH-:35].[Na+].OO>O1CCCC1>[C:1]([O:5][C:6]([C@@:8]12[CH2:14][C@H:13]([CH2:15][OH:35])[C@@H:12]1[CH2:11][N:10]([C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[CH2:9]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 67490991HCID 67490991, compound

Product 1

HCID 86664657HCID 86664657, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1S,5S)-3-Benzyloxycarbonyl-6-methylene-3-azabicyclo[3.2.0]heptane-1-carboxylic acid tert-butyl ester (2.00 g, 5.82 mmol) was dissolved in tetrahydrofuran (40 mL). A 9-borabicyclo[3.3.1]nonane dimmer (0.5 M solution in tetrahydrofuran) (17.5 mL, 8.73 mmol) was added dropwise, and then the mixture was stirred for two hours. A 3 M sodium hydroxide solution (3.49 mL, 10.5 mmol) and 30% aqueous hydrogen peroxide (2.47 mL) were added dropwise to the reaction solution at 0° C., and then the mixture was stirred at room temperature for 16 hours. The reaction solution was extracted with water and ethyl acetate. Then, the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=100:1→1:2) to give 1.58 g of an isomer A (less polar isomer) of the title compound and 50.0 mg of an isomer B (more polar isomer) of the title compound as colorless syrups.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. extractionThe reaction solution was extracted with water and ethyl acetate
  3. washThen, the organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20522f5495874b41b967cafc43c6f9fd
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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