Triphenylphosphine → 2-{2-[6-Nitro-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

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Reaction Steps

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one (13.5 g in 600 mL of N,N-dimethylformamide) was added 9.2 g of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid benzyl ester and 14 g of triphenylphosphine followed by 10.4 mL of diisopropyl azodicarboxylate and the mixture stirred at room temperature. After 24 hours, the solvents were removed in vacuo and the residue resolvated in methylene chloride, washed with water and purified by flash chromatography on silica gel (hexane:ethyl acetate, 90:10; then methylene chloride:ethyl acetate, 95:5) to give the title compound (13.2 g).

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