2-Fluoropyridine → Tert-butyl 4-cyano-4-(pyridin-2-YL)piperidine-1-carboxylate

Participants

Reaction Steps

A solution of 2-fluoropyridine (5.83 g, 60 mmol) and tert-butyl 4-cyanopiperidine-1-carboxylate (I-1, 4.22 g, 20 mmol) in toluene (40 mL) at room temperature was treated with KHMDS (48 mL of a 0.5 M solution, 24 mmol). After stirring 2 h, the reaction mixture was poured into brine (150 mL) and extracted with EtOAc (3×150 mL). The combined organic extracts were washed with brine (2×150 mL), dried (MgSO4), and concentrated under reduced pressure to afford tert-butyl 4-cyano-4-pyridin-2-ylpiperidine-1-carboxylate (I-2) as a yellow-brown solid. Analytical LCMS: single peak (214 nm), 3.076 min. This material was used in subsequent reactions without further purification.

Provenance & Evidence