Diethyl Ether → 2,2-Dimethyl-3-(pyridin-4-yl)propan-1-amine

HRID 18397ノート

反応式

HRID 18397 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH3:12][C:13]([CH3:34])([CH:16]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)OS(C1C=CC(C)=CC=1)(=O)=O)[C:14]#[N:15].[OH-].[Na+]>O1CCCC1.O>[CH3:12][C:13]([CH3:34])([CH2:16][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)[CH2:14][NH2:15]

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 219740222,2-Dimethyl-3-(4-pyridyl)-3-(p-tolylsulfonyloxy)propionitrile

生成物 1

HCID 121366422,2-Dimethyl-3-(pyridin-4-yl)propan-1-amine収率 28%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium aluminum hydride (345 mg, 9.10 mmol) was put under a nitrogen atmosphere, and anhydrous diethyl ether (10 ml) was added dropwise thereto under ice-cold water-cooling. Next, a solution of 2,2-dimethyl-3-(4-pyridyl)-3-(p-tolylsulfonyloxy)propionitrile (600 mg, 1.82 mmol) in tetrahydrofuran (10 ml) was added dropwise to the mixture. The whole was stirred at room temperature overnight, and water (324 μl), a 15% aqueous sodium hydroxide solution (324 μl) and water (972 μl) were added successively to the reaction mixture under ice-cold water-cooling while stirring it vigorously. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography to give the target compound (83.0 mg, 0.505 mmol, 28%) as a pale yellow oily matter.

後処理

  1. temperatureunder ice-cold water-cooling
  2. temperaturecooling
  3. stirringwhile stirring it vigorously
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationthe obtained concentrate
  7. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-4eb857f5e3144afe9cd71d3fb2559940
出典データセット
uspto-grants-2010_06
特許番号
US07741346B2

反応ノート

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