Ethanol → 3-(3-Hexyl-6-isopropyl-3-azabicyclo[3.1.0]hex-6-yl)aniline

HRID 428940ノート

反応式

HRID 428940 の反応式
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH:22]([CH3:24])[CH3:23])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(O)C.[Cl-].[Ca+2].[Cl-]>O.[Fe]>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[NH2:19])[CH:22]([CH3:24])[CH3:23])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

参加物

6

反応物 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 221411753-Hexyl-6-isopropyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane

生成物 1

HCID 221413693-(3-Hexyl-6-isopropyl-3-azabicyclo[3.1.0]hex-6-yl)aniline収率 104.8%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

To a stirred suspension of 3-hexyl-6-isopropyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane (Preparation 60, 0.18 g, 0.54 mmol), ethanol (15 ml) and iron powder (0.27 g, 4.88 mmol) was added calcium chloride (0.06 gmu 0.54 inmol) in water (3 ml). The reaction mixture was heated under reflux for 3 h and then filtered through a pad of Celite®, the mother liquors were concentrated in vacuo. The residue was dissolved in dichloromethane and filtered again through a Sep-Pak® Plus cartridge containing silica (1.5 g), (Water Division Millipore), to remove any residual iron salts and then concentrated to give the crude title compound as a yellow solid (0.17 g, 100%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 h
  3. filtrationfiltered through a pad of Celite®
  4. concentrationthe mother liquors were concentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane
  6. filtrationfiltered again through a Sep-Pak® Plus cartridge
  7. additioncontaining silica (1.5 g), (Water Division Millipore),
  8. customto remove any residual iron salts
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-68a489b6cfb546199f6670c1739a9155
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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