Water → HCID 23158240, compound

HRID 601687Notes

Reaction equation

HRID 601687 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][C:13]([OH:16])([CH3:15])[CH3:14])[CH2:5]2.[H-].[Na+].O.[O:20]1CC[CH2:22][CH2:21]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][C:13]([CH3:14])([O:16][C:21](=[O:20])[CH3:22])[CH3:15])[CH2:5]2

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 231582085-Bromo-2-(2-hydroxy-2-methylpropyl)-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 23158240HCID 23158240, compound

Procedure

Under nitrogen atmosphere, 50 mg of 5-bromo-2-(2-hydroxy-2-methyl-propyl)-1-oxo-isoindoline obtained in Example 177-1) was dissolved in tetrahydrofuran. 21 mg of acetatic anhydride and 20 mg of sodium hydride were added and the mixture was heated under reflux for 4 hours. The reaction solution was cooled down to room temperature, water was added and the products were extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by silicagel column chromatography (ethyl acetate/hexane=1/2) to obtain 44 mg of the above compound as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. extractionthe products were extracted with ethyl acetate
  4. washEthyl acetate layer was washed with saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationThe solvents were distilled outunder reduced pressure
  7. customthe residues were separated
  8. custompurified by silicagel column chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-b7e770eeefc04fca988962e23413f765
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

Loading…