Tert-butyl 3-cyano-3-(4-phenylpiperidin-1-yl)pyrrolidine-1-carboxylate → Tert-butyl 3-methyl-3-(4-phenylpiperidin-1-yl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

To a 0° C. solution of tert-butyl 3-cyano-3-(4-phenylpiperidin-1-yl)pyrrolidine-1-carboxylate (1.2 g, 3.38 mmol) in THF (16 mL) was added a solution of methylmagnesium bromide (1.4M in THF, 12.06 mL) dropwise. The mixture was stirred at ambient temperature for about 2.5 h, cooled to about 0° C. and quenched by the dropwise addition of saturated ammonium chloride solution. The organic phase was separated, washed with water (2×75 mL) and brine (50 mL), dried over magnesium sulfate and concentrated under reduced pressure to yield tert-butyl 3-methyl-3-(4-phenylpiperidin-1-yl)pyrrolidine-1-carboxylate (1.12 g, 3.25 mmol) as a yellow solid. HPLC (Table 1, Method f) Rt 5.01 min; m/z: (M+H)+ 345.

Provenance & Evidence