Sodium Bicarbonate → Methyl 1-[2-[4-(5-methylpyridin-2-ylamino)piperidin-1-yl]ethyl]cyclohexanecarboxylate

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To a solution of 2-(piperidin-4-ylamino)-5-methylpyridine (191 mg) and methyl 1-(2-oxoethyl)cyclohexanecarboxylate (250 mg) in tetrahydrofuran (10 mL) were added acetic acid (150 mg) and sodium triacetoxy borohydride (424 mg) at room temperature. The solution was stirred at room temperature for 20 hours. Saturated aqueous sodium bicarbonate solution was added to the solution, and it was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, ethyl acetate-methanol-aqueous ammonia (90:10:0.1)] to give the title compound (30 mg).

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