4-Toluenesulfonyl chloride → 1-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

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Reaction Steps

4-Methylbenzenesulfonyl chloride (52.1 g) was added to a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (50.0 g) in pyridine (248 mL) at room temperature. The mixture was stirred at room temperature overnight. After evaporation of the solvent, water and ethyl acetate were added to the residue. The organic layer was separated, washed with 1M hydrochloric acid and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was triturated in diisopropyl ether at 0 C (“C” represents “degrees Celsius”) to give the title compound (76.1 g).

Provenance & Evidence