Sodium Iodide → tert-Butyl 9-(pyridin-4-yloxy)-3-azaspiro[5.5]undecane-3-carboxylate

Participants

Reaction Steps

4-Chloropyridine hydrochloride (1.3 g) was added to sodium hydride (0.89 g) in DMSO (20 ml), and the mixture was stirred for 10 minutes. tert-Butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate (2.0 g) in DMSO (20 ml) was then added slowly, and the mixture was stirred overnight (TLC control, conversion about 30-35%). A catalytic amount of sodium iodide was added, and the reaction mixture was stirred for 8 hours at 80° C. (TLC monitoring). Methanol and NaHCO3 solution were added to the reaction mixture, and stirring was carried out for 20 minutes. The mixture was then extracted with ethyl acetate and washed again with NaHCO3 solution and cold water. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude product so obtained was purified by column chromatography (silica gel, 70% ethyl acetate/hexane). Yield: 1.0 g (40%)

Provenance & Evidence