Water → tert-Butyl 4-[(benzyloxy)methyl]-4-cyanopiperidine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-cyanopiperidine-1-carboxylate (4 g, 19 mmol) in THF (70 mL) cooled to 0° C. is added 0.5 M KHMDS (57 mL, 28.5 mmol) in toluene dropwise. The reaction mixture is warmed to room temperature and stirred for 1 h. Chloromethoxymethyl-benzene (4.46 g, 28.5 mmol) is added and the reaction mixture is stirred for another 1 h at room temperature. Water and ethyl acetate are added and the aqueous layer is separated and extracted with ethyl acetate (2×50 mL). The organic layers are combined, washed with brine, dried (Na2SO4) and concentrated to afford the title compound (3 g, 48.3%) as a light yellow liquid.

Provenance & Evidence