Water → HCID 23158256, compound

HRID 601689Notes

Reaction equation

HRID 601689 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+].[CH3:19]I.O>O1CCCC1>[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])([CH3:14])[CH3:15])[CH:5]2[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 231582085-Bromo-2-(2-hydroxy-2-methylpropyl)-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 23158256HCID 23158256, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, 100 mg of 5-bromo-2-(2-hydroxy-2-methyl-propyl)-1-oxo-isoindoline obtained in Example 177-1) was dissolved in tetrahydrofuran, 40 mg of sodium hydride, 0.4 ml of methyl iodide were added and the mixture was heated under reflux for 2 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 thin-layer silicagel column chromatography (ethyl acetate) to obtain 7 mg of the above compound as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 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 thin-layer silicagel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-bcc8016cf37b4092a55c768cb4784529
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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