反应详情

温度

60 °C

A mixed solution obtained by mixing 3.5 g of 79% pure (S)-1-benzyl-3-(1-cyano-1,1-diphenylmethyl)-pyrrolidine with 2.8 ml of ethanol and adding dropwise 0.72 ml of 35% aqueous hydrochloric acid thereto with cooling on an ice-water bath was charged, together with 139 mg of moist 5% palladium-carbon (water content 52% by weight), into an autoclave, hydrogen was introduced thereinto and the autoclave was heated to raise the temperature to 60° C. and the pressure to 203 kPa, and the reaction was allowed to proceed for 3 hours. Hydrogen absorption came to an end in 2.6 hours after the start of hydrogen introduction. After completion of the reaction, the reaction mixture was cooled to room temperature and depressurized. The reaction mixture was taken out, the catalyst was filtered off, the filtrate obtained was concentrated under reduced pressure, toluene and water were added to the thus-obtained oily concentrate, and the pH was adjusted to 13 by adding dropwise 30% aqueous sodium hydroxide with stirring on an ice-water bath. The toluene layer was recovered, the aqueous layer was further extracted with toluene, and the toluene layers were combined, washed with a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and, after filtration, concentrated under reduced pressure and further dried under vacuum to give 2.1 g of (S)-3-(1-cyano-1,1-diphenylmethyl)-pyrrolidine as an oil (yield: 91 mole percent).

1. customA mixed solution obtained
2. temperaturewith cooling on an ice-water bath
3. additionwas introduced
4. temperaturethe autoclave was heated
5. customHydrogen absorption
6. waitcame to an end in 2.6 hours
7. customAfter completion of the reaction
8. temperaturethe reaction mixture was cooled to room temperature
9. filtrationthe catalyst was filtered off
10. customthe filtrate obtained
11. concentrationwas concentrated under reduced pressure, toluene and water
12. additionwere added to the thus-obtained oily concentrate
13. additionby adding dropwise 30% aqueous sodium hydroxide
14. customThe toluene layer was recovered
15. extractionthe aqueous layer was further extracted with toluene
16. washwashed with a saturated aqueous solution of sodium chloride
17. dry with materialdried with anhydrous sodium sulfate
18. filtrationafter filtration
19. concentrationconcentrated under reduced pressure
20. customfurther dried under vacuum