Citric Acid → Methyl 2-hydroxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoate

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (0.31 g) and 1-(methylsulfonyl)piperidin-4-yl methanesulfonate (0.46 g) were added to an N,N-dimethylacetamide (5 mL) solution of methyl 2,4-dihydroxybenzoate (0.25 g), followed by stirring at 90° C. for 1 hour. The reaction mixture was cooled to room temperature, and then sodium iodide (0.045 g) was added thereto, followed by stirring at 90° C. for 1 hour. The reaction mixture was cooled to room temperature, and then potassium carbonate (0.10 g) and 1-(methylsulfonyl)piperidin-4-yl methanesulfonate (0.12 g) were added thereto, followed by stirring at 90° C. for 1 hour. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were added thereto. The organic layer was separated, washed with a 10% aqueous solution of citric acid and saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-60% hexane/ethyl acetate] to obtain 0.19 g of methyl 2-hydroxy-4-((1-(methylsulfonyl)piperidin-4-yl)oxy)benzoate as a white solid.

Provenance & Evidence