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

Temperature

40 °C

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%).

1. customUpon completion, the reaction was then quenched by the addition of aqueous NaHCO3 (200 mL)
2. extractionThe resulting mixture was extracted with dichloromethane (4×100 mL)
3. washCombined organic layers were washed with brine (1×30 mL)
4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
5. concentrationconcentrated on a rotary evaporator
6. customThe residue was purified by silica gel column chromatography
7. washeluted with ethyl acetate/petroleum ether (1:10-1:2)

ORD record

ord-ea5d232ac69747328f2619fa5e09b781

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080566B1