1-Chloroethyl chloroformate → 2,6-Bis(trifluoromethyl)-4-[3-(trifluoromethyl)pyrrolidin-3-yl]pyridine

HRID 2206926

반응식

HRID 2206926 반응식
C([N:8]1[CH2:12][CH2:11][C:10]([C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)([C:13]([F:16])([F:15])[F:14])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[F:30][C:27]([F:28])([F:29])[C:19]1[CH:18]=[C:17]([C:10]2([C:13]([F:14])([F:15])[F:16])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[N:20]=1

참가 물질

4

반응물 2

HCID 5213051-Chloroethyl chloroformateHCID 866749264-[1-Benzyl-3-(trifluoromethyl)pyrrolidin-3-yl]-2,6-bis(trifluoromethyl)pyridine

생성물 1

HCID 532621872,6-Bis(trifluoromethyl)-4-[3-(trifluoromethyl)pyrrolidin-3-yl]pyridine수율 70.1%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

The solution of 4-[1-benzyl-3-(trifluoromethyl)pyrrolidin-3-yl]-2,6-bis(trifluoromethyl)pyridine (1.4 g) and 1-chloroethyl chloroformate (0.905 g) in dichloroethane was heated to reflux for 3 hours. The mixture was cooled to room temperature and then concentrated under the reduced pressure. Methanol was added to the resultant residue, which was then heated with stirring at 60° C. for two hours. The mixture was cooled to room temperature, to which was then added water. The solution was washed twice with the mixed solvent of hexane. The solution was neutralized with sodium hydroxide and then extracted with tert-butyl methyl ether three times. The organic layer was combined, which was then washed with brine and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure to yield 2,6-bis(trifluoromethyl)-4-[3-(trifluoromethyl)pyrrolidin-3-yl]pyridine (0.781 g).

후처리

  1. temperatureto reflux for 3 hours
  2. concentrationconcentrated under the reduced pressure
  3. additionMethanol was added to the resultant residue, which
  4. temperaturewas then heated
  5. temperatureThe mixture was cooled to room temperature, to which
  6. washThe solution was washed twice with the mixed solvent of hexane
  7. extractionextracted with tert-butyl methyl ether three times
  8. washwhich was then washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter the drying agent was filtered off
  11. distillationthe solvent was distilled away under the reduced pressure

출처 및 근거

ORD 기록
ord-002d6c4a3e964379adeaa82ba2e28be8
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09375000B2

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