Potassium Carbonate → trans-2-[(2-hydroxycyclohexyl)methyl]-1H-isoindole-1,3(2H)-dione

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Reaction Steps

Under a nitrogen atmosphere, a solution of trans-2-cyanohexanol (1.0 g, 7.99 mmol) in tetrahydrofuran (10 ml) was added dropwise to a solution of lithium aluminum hydride (1.21 g, 0.0320 mol) in tetrahydrofuran (15 ml) at 0° C., and the resulting mixture was refluxed. After 2 hours, water, a 2M-aqueous sodium hydroxide solution and water were added in that order to the reaction solution, and the resulting mixture was filtered by the use of Celite. To the filtrate was added 1M-hydrochloric acid-diethyl ether (9.59 ml, 9.59 mmol), and the resulting mixture was concentrated under reduced pressure. Potassium carbonate (1.99 g, 0.0144 mol) and ethoxycarbonylphthalimide (1.93 g, 8.79 mmol) were added to an aqueous solution (30 ml) of the concentration residue at room temperature. After 15 hours, the reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain trans-2-[(2-hydroxycyclohexyl)methyl]-1H-isoindole-1,3(2H)-dione (1.1736 g, 57%).

Provenance & Evidence