Sodium hydride → HCID 90065712, compound

Participants

Reaction Steps

After 60% sodium hydride (17 mg) was added to a solution of tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (109 mg) in DMF (2 mL) at 0° C. in a nitrogen atmosphere, the mixture was stirred at room temperature for 30 minutes. After the reaction mixture was cooled to 0° C., 4-bromo-1-fluoro-2-(methylsulfonyl)benzene (100 mg) was added thereto. The reaction mixture was stirred at 0° C. for 30 minutes, and stirred at room temperature for 3 hours. After a saturated aqueous ammonium chloride solution was added to the reaction mixture, extraction thereof was performed using EtOAc, and the extract was washed with water and saturated brine. The organic layer was dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=80:20 to 55:45), whereby tert-butyl 4-{2-[4-bromo-2-(methylsulfonyl)phenoxy]ethyl}piperidine-1-carboxylate (169 mg) was obtained as a colorless liquid.

Provenance & Evidence