Water → 10-Benzyl-3,10-diazabicyclo[4.3.1]decane

HRID 1912339

反応式

HRID 1912339 の反応式
[CH2:1]([N:8]1[CH:14]2[CH2:15][CH2:16][CH2:17][CH:9]1[CH2:10][NH:11][C:12](=O)[CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.ClCCl>[CH2:1]([N:8]1[CH:14]2[CH2:15][CH2:16][CH2:17][CH:9]1[CH2:10][NH:11][CH2:12][CH2:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 4579274510-Benzyl-3,10-diazabicyclo[4.3.1]decan-4-one

生成物 1

HCID 4579275510-Benzyl-3,10-diazabicyclo[4.3.1]decane

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution obtained by dissolving 0.50 g of 10-benzyl-3,10-diazabicyclo[4.3.1]decan-4-one (1py1) in THF (4 ml) is dripped in a suspension of LiAlH4 (0.19 g) in anhydrous THF (9 ml), cooled at 0° C., kept under an argon inert atmosphere. The mixture is kept under stirring at room temperature for 14 hours. At the end the mixture is cooled to 0° C. About 0.9 ml of H2O are cautiously added while stirring for 10 min. A precipitate is obtained which is filtered under vacuum and washed with dichloromethane. The recovered filtrate is evaporated, obtaining an oil which is dissolved in dichloromethane. The organic solution is dehydrated with sodium sulphate and the solvent then evaporated. 0.47 g of the compound 10-benzyl-3,10-diazabicyclo[4.3.1]decane are recovered. Yield: quantitative; Rf: 0.62 (CH2Cl2-MeOH 8:2); 1H-NMR (CDCl3): δ (ppm) 1.17-2.18 (m, 8H), 2.62 (bs, 1H), 2.76-2.92 (m, 2H), 2.99-3.18 (m, 4H), 3.97 (s, 2H), 7.20-7.42 (m, 5H).

後処理

  1. customA solution obtained
  2. temperatureAt the end the mixture is cooled to 0° C
  3. stirringwhile stirring for 10 min
  4. customA precipitate is obtained which
  5. filtrationis filtered under vacuum
  6. washwashed with dichloromethane
  7. customThe recovered filtrate is evaporated
  8. customobtaining an oil which
  9. customthe solvent then evaporated
  10. custom0.47 g of the compound 10-benzyl-3,10-diazabicyclo[4.3.1]decane are recovered

出典と根拠

ORDレコード
ord-038f332a90af4106abb3d7f44c0cf0c5
出典データセット
uspto-grants-2013_12
特許番号
US08609659B2

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