Water → HCID 89500577, compound

Participants

Reaction Steps

Potassium tert-butoxide (1M in THF, 14.4 ml, 14.4 mmol, 5 eq) and 2,5-difluoropyridine (498.3 mg, 4.33 mmol, 1.5 eq) are added to a mixture of tert-butyl 3-hydroxyazetidine-1-carboxylate a1-47 (500 mg, 2.89 mmol, 1 eq) in DMSO (50 ml). The reaction is stirred for 4 h at room temperature. Brine (70 ml) and water (10 ml) are added. The resulting mixture is extracted with ethyl acetate (3×50 ml). The combined organic phases are dried over MgSO4, filtered and concentrated in vacuo. The residue of evaporation is purified by flash chromatography over silicagel (eluent: EtOAc/Heptane 10/90) to afford 240 mg of tert-butyl 3-[(5-fluoropyridin-2-yl)oxy]azetidine-1-carboxylate a1-48.

Provenance & Evidence