Phosphoric Acid → 1-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

Participants

Reaction Steps

To a solution of p-toluenesulfonylchloride (6.42 g, 33.69 mmol) in CH2Cl2 (45 mL) and N,N-dimethylformamide (5 mL), chilled to 0° C., was added triethylamine (7.2 mL, 51.66 mmol), dimethylaminopyridine (275 mg, 2.25 mmol) and then dropwise addition of N-Boc-4-hydroxypiperidine (4.52 g, 22.46 mmol) in CH2Cl2 (45 mL). The resulting mixture was stirred for 3 days and then added 1M H3PO4 (40 mL), separated the layers and extracted with CH2Cl2 (50 mL). The organic layers were combined, washed with NaHCO3 (aq) (40 mL), brine (40 mL), dried over MgSO4, filtered and concentrated to provide a crude solid which was purified by flash column chromatography (7 to 60% EtOAc/Heptane) to provide 6.21 g (78% yield) of the title compound as a solid.

Provenance & Evidence