Sodium hydride → HCID 21906105, compound

Participants

Reaction Steps

To a slurry of sodium hydride (about 60% oil suspension, 114 mg) in dimethyl sulfoxide (5 ml) was added dropwise tert-butyl 4-hydroxy-1-piperidinecarboxylate (576 mg). Considerable foaming occurred and the solution turned pale orange. To this solution was added chloropyrazine (377 mg) and the mixture was stirred at room temperature for 12 hours. The resulting mixture was partitioned between saturated aqueous sodium hydrogencarbonate solution and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residual solid was triturated with a mixture of ethyl acetate and n-hexane to give the title compound (472 mg) as white crystals.

Provenance & Evidence