Acrolein → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-(2-formylethyl)piperazine

HRID 584201노트

반응식

HRID 584201 반응식
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7].N12CCCN=C1CCCCC2.[CH:43]([CH:45]=[CH2:46])=[O:44]>O1CCCC1.O>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:46][CH2:45][CH:43]=[O:44])[CH2:10][C@H:9]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([CH3:22])[CH:16]=1)=[O:7]

참가 물질

6

반응물 3

HCID 7847AcroleinHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54478438(2R)-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine

생성물 1

HCID 86588518(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-(2-formylethyl)piperazine

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-30 °C

실험 절차

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)piperazine (500 mg) and 1,8-diazabicyclo [5.4.0]undec-7-ene (1.5 μl) in tetrahydrofuran (2.5 ml) was cooled to −30° C. with stirring under nitrogen atmosphere. Acrolein (90%, 0.225 ml) was added to the mixture while maintaining the temperature at −20˜−40° C. for a period of 10 minutes and then the resulting mixture was stirred at 0° C. After 6 hours, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. After evaporation of the solvent under reduced pressure, the resulting residue was chromatographed on a silica gel using a mixture of hexane and ethyl acetate as eluent to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-(2-formylethyl)piperazine (332 mg) as an oil.

후처리

  1. temperaturewhile maintaining the temperature at −20˜−40° C. for a period of 10 minutes
  2. stirringthe resulting mixture was stirred at 0° C
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent under reduced pressure
  7. customthe resulting residue was chromatographed on a silica gel using
  8. additiona mixture of hexane and ethyl acetate as eluent

출처 및 근거

ORD 기록
ord-2c3aa96a85014ab79231ed08da579b12
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924278B2

반응 노트

불러오는 중…