反应详情

To a solution of 2-{2-[6-allyl-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (EXAMPLE 4.1 Step E, 6.0 g in a mixture of 80 mL tert-butanol, 24 mL tetrahydrofuran and 8 mL water) was added 1.4 g 4-methylmorpholine N-oxide followed by 140 mg osmium tetraoxide and the mixture stirred at room temperature. After 20 hours, the mixture was concentrated in vacuo and the residue dissolved in ethyl acetate and washed sequentially with water and brine. The combined organics were dried over sodium sulfate and purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:1; then methylene chloride:10% ammonium hydroxide in methanol, 9:1) to give the title compound (5.7 g).

1. concentrationthe mixture was concentrated in vacuo
2. dissolutionthe residue dissolved in ethyl acetate
3. washwashed sequentially with water and brine
4. dry with materialThe combined organics were dried over sodium sulfate
5. custompurified by flash chromatography on silica gel (ethyl acetate