Sodium hydride → tert-Butyl 4-((6-chloropyrazin-2-yl)oxy)piperidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (3.80 g, 18.9 mmol) in DMF (76 ml) was added sodium hydride (60% mineral oil dispersion; 0.906 g, 22.7 mmol) at 0° C. The reaction mixture was stirred for 1 hour, until hydrogen evolution ceased. 2,6 dichloropyrazine (2.81 g, 18.9 mmol) was added, and the reaction mixture was allowed to warm to room temperature. After 1 hour, the reaction was quenched with brine (100 mL) and extracted with EtOAc (2×200 mL). The combined EtOAc layers were dried over magnesium sulfate, filtered and concentrated to a crude residue that was purified by silica gel chromatography (EtOAc/Hexanes gradient) to afford tert-butyl 4-[(6-chloropyrazin-2-yl)oxy]piperidine-1-carboxylate as a yellow solid. LRMS calculated for C14H20ClN3O3 [M+Na]+, 336.1; found 336.1.

Provenance & Evidence