Water → tert-Butyl 4-((5-bromopyridin-2-yl)oxy)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 4-hydroxytetrahydro-1(2H)-pyridinecarboxylate (10.0 g, 50.0 mmol) was dissolved in DMF (150 mL), and with stirring at 0° C., sodium hydride (purity 60%, 1.43 g) was added thereto. After stirred for 10 minutes, 4-bromo-2-fluoropyridine (8.75 g, 50.0 mmol) was added thereto and further stirred at room temperature for 20 hours. Water was added to the reaction solution and stirred for 10 minutes, and then the reaction solution was diluted with ethyl acetate, washed with water and saturated saline water in that order, and the organic layer was dried with magnesium sulfate. The solvent was evaporated off, and the residue was recrystallized from ethanol-water to obtain the intended compound (11 g) as a colorless solid.

Provenance & Evidence