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

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Reaction Steps

A mixture of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (11.6 g), tosyl chloride (11.44 g), and pyridine (60 mL) was stirred at room temperature for over-night. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate layer was washed with 1 M hydrochloric acid solution, water, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (16.94 g, 85%) as an oil.

Provenance & Evidence