反应详情

温度

5 °C

1-Benzyloxycarbonyl-3,3-dimethyl-4-piperidone (290 g, 1.11 mol) was dissolved in methanol (1.5 L) and under stirring addition of ammonium acetate (600 g, 7.80 mol ) was made at 30-35° C. The reaction mixture was stirred for 5 hrs. Sodium cyanoborohydride (35 g, 0.55 mol) was added portion wise to the suspension. over 0.5 hrs by maintaining temperature between 0-10° C. The reaction mixture was stirred for 6-7 hrs. After completion of reaction, solvent was evaporated under reduced pressure and addition of 3.00 L water was made under stirring. The reaction mixture was stirred for 15 minutes. It was extracted with 1.5 L×2 CHCl3. Combined organic extract was evaporated under vacuum. The residue was dissolved in 3 N HCl till pH 1 and was extracted with 500 ml×2 dichloromethane. The aqueous layer was basified with 300 ml aqueous ammonia solution (23-25%) to pH 10-11 and then was extracted with 1.5 L×3 dichloromethane. Combined organic extract was washed with water and was dried over sodium sulfate. Evaporation of organic solvent afforded 225 g (77%) title compound.

1. customwas made at 30-35° C
2. stirringThe reaction mixture was stirred for 5 hrs
3. stirringThe reaction mixture was stirred for 6-7 hrs
4. customAfter completion of reaction, solvent
5. customwas evaporated under reduced pressure and addition of 3.00 L water
6. stirringunder stirring
7. stirringThe reaction mixture was stirred for 15 minutes
8. extractionIt was extracted with 1.5 L×2 CHCl3
9. extractionCombined organic extract
10. customwas evaporated under vacuum
11. dissolutionThe residue was dissolved in 3 N HCl till pH 1
12. extractionwas extracted with 500 ml×2 dichloromethane
13. extractionwas extracted with 1.5 L×3 dichloromethane
14. extractionCombined organic extract
15. washwas washed with water
16. dry with materialwas dried over sodium sulfate
17. customEvaporation of organic solvent