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

HRID 1500196ノート

反応式

HRID 1500196 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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 layers were combined, washed with brine and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was removed under reduced pressure to yield 2,6-bis(trifluoromethyl)-4-[3-(trifluoromethyl)pyrrolidin-3-yl]pyridine (0.781 g).

後処理

  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. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationAfter the drying agent was filtered off
  11. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-82dc708fb22f41fa9aab6d2cfc2d3b49
出典データセット
uspto-grants-2015_12
特許番号
US09206122B2

反応ノート

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