反应详情

To 5-methylidene-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.60 g) are added successively t-butyl alcohol (6.0 ml), water (1.2 ml), pyridine (0.3 ml), osmium tetroxide (1.2 mg) and trimethylamine N-oxide dihydrate (0.22 g), and the mixture is refluxed with stirring for 2.5 hours. After cooling, to the reaction solution is added 20% aqueous sodium hydrogensulfite solution (10 ml), and the mixture is stirred at room temperature for 1.5 hour. The reaction solution is extracted with a mixture of ethyl acetate/tetrahydrofuran (1:1). The extract is washed successively with diluted hydrochloric acid and saturated saline solution, and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is recrystallized from ethyl acetate/n-hexane to give 5-hydroxymethyl-5-hydroxy-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.55 g) as white powder, m.p. 136°-140° C.

1. temperaturethe mixture is refluxed
2. temperatureAfter cooling, to the reaction solution
3. stirringthe mixture is stirred at room temperature for 1.5 hour
4. extractionThe reaction solution is extracted with a mixture of ethyl acetate/tetrahydrofuran (1:1)
5. washThe extract is washed successively with diluted hydrochloric acid and saturated saline solution
6. dry with materialdried over magnesium sulfate
7. distillationThe solvent is distilled off
8. customthe resulting residue is recrystallized from ethyl acetate/n-hexane