Allyl bromide → 1-tert-Butyl 4-methyl 4-allylpiperidine-1,4-dicarboxylate

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To a −78° C. solution of N-Boc-4-piperidinecarboxylic acid methyl ester (5.70 g, 23.4 mmol) in THF (80 mL) was added potassium hexamethyldisilazide (0.5 M in toluene, 70.2 mL, 35.1 mmol). After 2 h allyl bromide (6.69 mL, 77.3 mmol) was added, the reaction stirred at this temperature for 0.5 h, then warmed to 0° C. After 3 h the reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with dichloromethane (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of 0 to 8% methanol:dichloromethane to give the title compound (6.0 g). MS: m/z=284.2 (M+1).

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