反应详情

3.40 g (7.20 mmol) of (3R,4R)-3-hydroxy-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butylester and 2.18 g (7.20 mmol) of 7-bromomethyl-quinoline hydrobromide (1:1) [J. Am. Chem. Soc. 77, 1054(1955)], were dissolved in 50 ml of absolute dimethylformamide under argon and then 0.83 g (19.0 mmol) of sodium hydride dispersion (55% in mineral oil) was added at room temperature in small portions. Subsequently, the mixture was stirred at room temperature for 16 hours. The reaction mixture was poured onto ice-water, the product was extracted 3 times with ethyl acetate, the combined organic phases were washed twice with distilled water, then dried over magnesium sulphate, filtered and concentrated. The crude product (5.2 g, yellow oil) was chromatographed on silica gel with ethyl acetate/hexane 2:1 to yield 3.77 g (85.4% of theory) of (3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(quinolin-7-yl-methoxy)-piperidine-1-carboxylic acid tert-butylester as a colourless oil; MS: 613 (M+H)+.

1. additionThe reaction mixture was poured onto ice-water
2. extractionthe product was extracted 3 times with ethyl acetate
3. washthe combined organic phases were washed twice with distilled water
4. dry with materialdried over magnesium sulphate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude product (5.2 g, yellow oil) was chromatographed on silica gel with ethyl acetate/hexane 2:1