反应详情

温度

5 °C

76.2 g (0.445 mol) of 4-bromotoluene and 10.8 g (0.445 mol) of magnesium turnings in 500 cm3 of diethyl ether are heated at reflux for one hour. After cooling to a temperature in the region of 5° C., a solution of 124.65 g (0.343 mol) of levorotatory enantiomer methyl (3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenylperhydroisoindole-3a-carboxylate in 500 cm3 of toluene is added. The reaction mixture is stirred for one hour at a temperature in the region of 20° C. and then hydrolyzed with 450 cm3 of a saturated aqueous ammonium chloride solution. The aqueous phase is separated by settling and extracted with two times 500 cm3 of ethyl acetate. The organic phases are combined, washed successively with 100 cm3 of distilled water and 100 cm3 of a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. After purification by flash chromatography on silica gel (230-400 mesh), elution being carried out with cyclohexane/ethyl acetate (95/5 and then 80/20 by volume) mixtures, 135.9 g (87%) of the levorotatory enantiomer of methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-(4-methylphenyl)-4-phenylperhydroisoindole-3a-carboxylate are obtained in the form of a white solid, the characteristics of which are as follows:

1. temperatureat reflux for one hour
2. customThe aqueous phase is separated
3. extractionextracted with two times 500 cm3 of ethyl acetate
4. washwashed successively with 100 cm3 of distilled water and 100 cm3 of a saturated aqueous sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customAfter purification by flash chromatography
8. washon silica gel (230-400 mesh), elution