反应详情

温度

60 °C

5.1 cm3 of 4-bromotoluene and 1 g of magnesium turnings in 100 cm3 of diethyl ether were heated at reflux for one hour. 100 cm3 of toluene were added and the mixture was heated to 60° C. under a stream of nitrogen. After cooling to a temperature in the region of 5° C., a solution of 10 g of methyl (3aRS,4SR,7aRS)-2-benzyl-7-oxo-4-phenyloctahydroisoindole-3a-carboxylate in 80 cm3 of toluene was added. The reaction mixture was stirred for one hour at a temperature in the region of 20° C. and then hydrolysed with 100 cm3 of a saturated aqueous ammonium chloride solution. The aqueous phase was separated by settling and extracted with two times 75 cm3 of ethyl acetate. The organic phases were combined, washed successively with 100 cm3 of distilled water and 100 cm3 of a saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. After purification by flash chromatography on silica gel (230-400 mesh), elution was carried out with a cyclohexane/ethyl acetate (80/20 by volume) mixture, 9 g of methyl (3aRS,4SR,7RS,7aRS)-2-benzyl-7-hydroxy-7-(4-methylphenyl)-4-phenyloctahydroisoindole-3a-carboxylate were obtained in the form of a white solid, the characteristics of which were as follows:

1. temperatureat reflux for one hour
2. temperatureAfter cooling to a temperature in the region of 5° C.
3. customThe aqueous phase was separated
4. extractionextracted with two times 75 cm3 of ethyl acetate
5. washwashed successively with 100 cm3 of distilled water and 100 cm3 of a saturated aqueous sodium chloride solution
6. dry with materialdried over magnesium sulphate
7. concentrationconcentrated under reduced pressure
8. customAfter purification by flash chromatography
9. washon silica gel (230-400 mesh), elution