Pyridine → Tert-butyl 3-[(4-nitrophenyl)sulfonyloxy]piperidine-1-carboxylate

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A 500-mL round-bottomed flask was charged with a solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (16 g, 79.60 mmol, 1.00 equiv) in DCM (200 mL), 4-nitrobenzene-1-sulfonyl chloride (17.6 g, 79.64 mmol, 1.00 equiv) and pyridine (9 mL). The resulting solution was stirred at 40° C. for 16 hours. The reaction progress was monitored by TLC (EtOAc: PE=1:2). Upon completion, the reaction was then quenched by the addition of aqueous NaHCO3 (200 mL). The resulting mixture was extracted with dichloromethane (4×100 mL). Combined organic layers were washed with brine (1×30 mL). The organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator. The residue was purified by silica gel column chromatography eluted with ethyl acetate/petroleum ether (1:10-1:2) affording tert-butyl 3-(4-nitrophenylsulfonyloxy)piperidine-1-carboxylate as yellow solid (23 g, 75%).

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