Potassium Carbonate → Isopropyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A stirring mixture of 4-hydroxypyridin-2(1H)-one (1.5 g, 13.5 mmol), isopropyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (5.0 g, 18.9 mmol, prepared according to the procedure described in Step C of Example 1) and potassium carbonate (3.7 g, 27.0 mmol, EMD) in DMF (80 mL) was heated at 140° C. for 2 h and then cooled to room temperature. The resulting mixture was diluted with EtOAc and H2O and the aqueous layer was extracted further with EtOAc (7×). The combined extracts were washed with saturated NH4Cl aqueous solution (2×), dried (Na2SO4) and evaporated. The residual was purified by flash chromatography (0 to 100% EtOAc/Hexanes and then 5% MeOH/CH2Cl2) to yield 1.67 g (44%) of the product as an off-white solid. MS (ESI) 281 (M+H).

Provenance & Evidence