2-Cyclopentyl-5-hydroxyisoindoline-1,3-dione → 2-Cyclopentyl-5-hydroxyisoindolin-1-one

HRID 404955Notes

Reaction equation

HRID 404955 reaction equation
[CH:1]1([N:6]2[C:14](=O)[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=3)[C:7]2=[O:17])[CH2:5][CH2:4][CH2:3][CH2:2]1>CC(O)=O.[Zn]>[CH:1]1([N:6]2[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=3)[C:7]2=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 138973992-Cyclopentyl-5-hydroxyisoindoline-1,3-dione

Product 1

HCID 509936542-Cyclopentyl-5-hydroxyisoindolin-1-oneYield 44%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-cyclopentyl-5-hydroxyisoindoline-1,3-dione (4.1 g, 18.0 mmol), in CH3CO2H (129 mL), Zn dust (11.6 g, 180 mmol) was added and the mixture heated at reflux for 5 min. The volatiles were removed in vacuo and the residue was dissolved in water and extracted with ethyl acetate. The crude residue was purified using automated prep-HPLC to yield the desired compound (1.7 g, 44%) as a white solid. 1HNMR (400 MHz, DMSO-d6): 10.10 (bs, 1H), 7.44 (d, J=8.5 Hz, 1H), 6.89 (s, 1H), 6.83 (d, J=7.9 Hz, 1H), 4.52-4.48 (m, 1H), 4.31 (s, 2H), 1.83-1.57 (m, 8H). LCMS calcd for C13H15NO2 [M+H]+ 218 found: 218.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 5 min
  3. customThe volatiles were removed in vacuo
  4. dissolutionthe residue was dissolved in water
  5. extractionextracted with ethyl acetate
  6. customThe crude residue was purified

Sources & evidence

ORD record
ord-7dd72f917c5a4be98906a7868b648cbc
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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