Ethanol → 1-(4-Ethoxycarbonyl-1,3-thiazol-2-yl)4-methanesulfonyloxypiperidine

Participants

Reaction Steps

To a solution of 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-4-hydroxypiperidine (128 mg, 0.50 mmol) (obtained as described in Reference Example 13(2)) in methylene chloride (6.5 ml) was added methanesulfonyl chloride (0.043 ml, 0.56 mmol) and triethylamine (0.084 ml, 0.60 mmol) in an ice bath. The reaction mixture was brought to room temperature in 10 minutes and then stirred for 30 minutes. After checking the completion of the reaction, ethanol (1 ml) was added thereto in an ice bath and then the reaction mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was recrystallized from a solution of ethyl acetate:n-hexane (5:1) to afford 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)4-methanesulfonyloxypiperidine (81.0 mg, yield 49%) as a white solid.

Provenance & Evidence