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0 °C

To a suspension of trans-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4,4-dimethylcyclohexyl 4-nitrobenzoate (420 mg, 1.00 mmol) in a mixture of methanol (0.10 ml) and tetrahydrofuran (10 ml) was added 28%-sodium methoxide (0.24 ml, 1.00 mmol) at 3° C., and stirred at 0° C. for 30 minutes and then at room temperature for 35 minutes. The reaction solution was adjusted to pH 4 with a 0.5M-aqueous potassium hydrogensulfate solution and then distilled under reduced pressure to remove the solvent. The residue was added to water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain trans-2-(5-hydroxy-2,2-dimethylcyclohexyl)-1H-isoindole-1,3(2H)-dione (231 mg, 85%).

1. waitat room temperature for 35 minutes
2. distillationdistilled under reduced pressure
3. customto remove the solvent
4. additionThe residue was added to water
5. extractionextracted with ethyl acetate
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. distillationdistilled under reduced pressure
8. customto remove the solvent
9. customthe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=2/1)