Potassium Phosphate, Tribasic → 1-[5-(2-Ethoxy-2-oxoethoxy)-6-nitropyridin-2-yl]-5-oxopyrrolidin-3-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-oxopyrrolidin-3-carboxylic acid methyl ester (synthesized with reference to Tetrahedron Asymmetry, 2001, vol. 12, pages 3241-3250; 1.0 g, 6.99 mmol), [(6-bromo-2-nitropyridin-3-yl)oxy]acetic acid ethyl ester (synthesized with reference to WO2004/2992; 2.13 g, 6.99 mmol), palladium acetate (157 mg, 0.699 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (417 mg, 0.699 mmol), potassium phosphate (4.83 g, 21 mmol) and 1,4-dioxane (50 ml) was stirred under a stream of nitrogen gas at 100° C. for 5 hours. After cooling, ethyl acetate was added to the reaction solution, the insoluble material was removed by filtration, the obtained filtrate was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 1.95 g (76%) of the title compound in the form of a light brown syrup.

Provenance & Evidence