Calcium Chloride → 3-Hexyl-6-(3-aminophenyl)-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 428967ノート

反応式

HRID 428967 の反応式
[CH2:1]([N:7]1[C:12](=[O:13])[CH:11]2[CH:9]([C:10]2([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=2)[CH2:14][C:15]([F:18])([F:17])[F:16])[C:8]1=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl-].[Ca+2].[Cl-]>C(O)C.O.[Fe]>[CH2:1]([N:7]1[C:8](=[O:28])[CH:9]2[CH:11]([C:10]2([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=2)[CH2:14][C:15]([F:16])([F:17])[F:18])[C:12]1=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

参加物

6

反応物 2

HCID 5284359Calcium ChlorideHCID 221412833-Hexyl-6-(3-nitrophenyl)-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

生成物 1

HCID 221411683-Hexyl-6-(3-aminophenyl)-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hexane-2,4-dione収率 102.5%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

3-Hexyl-6-(3-nitrophenyl)-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hexane-2,4-dione (Preparation 103, 178 mg, 0.45 mmol) was dissolved in ethanol (15 ml). Iron powder (225 mg, 4.0 mmol) was added at room temperature followed by calcium chloride (50 mg, 0.45 mmol), dissolved in water (2 ml). The vigorously stirred mixture was heated under reflux for 2 h then cooled to room temperature and filtered through a pad of silica. The solvent was removed in vacuo and the filtrate was dissolved in dichloromethane and filtered through a Whatman anotop 10 plus™ cartridge. The organic mixture was concentrated in vacuo to give the product as a brown gum (170 mg, 100%).

後処理

  1. temperatureThe vigorously stirred mixture was heated
  2. temperatureunder reflux for 2 h
  3. filtrationfiltered through a pad of silica
  4. customThe solvent was removed in vacuo
  5. dissolutionthe filtrate was dissolved in dichloromethane
  6. filtrationfiltered through a Whatman anotop 10 plus™ cartridge
  7. concentrationThe organic mixture was concentrated in vacuo

出典と根拠

ORDレコード
ord-b759ef81c710456c983dcd07ee816c82
出典データセット
uspto-grants-2001_11
特許番号
US06313312B1

反応ノート

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