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

Participants

Reaction Steps

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.

Provenance & Evidence