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

HRID 584201ノート

反応式

HRID 584201 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2c3aa96a85014ab79231ed08da579b12
出典データセット
uspto-grants-2005_08
特許番号
US06924278B2

反応ノート

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