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

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Reaction Steps

To a stirred solution of 1-boc-4-hydroxypiperidine (3.80 g, 18.9 mmol) in DMF (76 mL) at 0° C. was added sodium hydride (60% mineral oil dispersion; 0.906 g, 22.7 mmol). Once hydrogen evolution had ceased, 2,6-dichloropyrazine (2.81 g, 18.9 mmol) was added and the reaction mixture was allowed to warm to ambient temperature. After 1 h, the reaction mixture was quenched with brine (100 mL) and extracted with EtOAc (2×100 mL). The combined organics were dried over magnesium sulfate, filtered and concentrated. The crude residue 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 (ESI) calculated for C14H20ClN3O3 336.1; found [M+Na]+, 336.1.

Provenance & Evidence