Water → 9-Methyl-3,9-diazabicyclo[4.2.1]nonane

HRID 1946853

反応式

HRID 1946853 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][NH:11][C:12](=O)[CH2:13]2.O>C1COCC1.ClCCl>[CH3:7][N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][NH:11][CH2:12][CH2:13]2

参加物

6

反応物 3

HCID 962Water2 回HCID 5574669-Methyl-3,9-diazabicyclo(4.2.1)nonan-4-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 139737309-Methyl-3,9-diazabicyclo[4.2.1]nonane収率 69%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

To a suspension of LiAlH4 (0.61 g) in anhydrous THF (30 ml), cooled at 0° C., and kept under an argon inert atmosphere, a solution in THF of 9-methyl-3,9-diazabicyclo[4.2.1]nonan-4-one obtained in example 1 is dropwise added (1.00: of compound in 10 ml of THF). The obtained mixture is heated at reflux for 48 hours and then cooled at 0° C. Then water (3 ml) is slowly added to the mixture. After water addition, the mixture is kept under stirring for 1:0 minutes. A precipitate is formed, that at the end is filtered under vacuum and washed with dichloromethane. The obtained filtrate is evaporated obtaining an oil which is dissolved in dichloromethane. The obtained solution is then anhydrified on sodium sulphate and the solvent evaporated. The residual oil is distilled (45-50° C./0.1 mmHg) to give 0.63 g of 9-methyl-3,9-diazabicyclo[4.2.1]nonane (2a) as a colourless oil.

後処理

  1. temperatureThe obtained mixture is heated
  2. temperatureat reflux for 48 hours
  3. temperaturecooled at 0° C
  4. custom0 minutes
  5. customA precipitate is formed, that at the end
  6. filtrationis filtered under vacuum
  7. washwashed with dichloromethane
  8. customThe obtained filtrate is evaporated
  9. customobtaining an oil which
  10. customthe solvent evaporated
  11. distillationThe residual oil is distilled (45-50° C./0.1 mmHg)

出典と根拠

ORDレコード
ord-1182d64edc7f4c0bab5e87d3d759b2fd
出典データセット
uspto-grants-2013_03
特許番号
US08399457B2

関連ノート

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