Water → Piperidin-3-yl-trityl-amine

HRID 2212178ノート

反応式

HRID 2212178 の反応式
[C:1]([NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][C:22]1=O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[NH:23]1[CH2:24][CH2:25][CH2:26][CH:21]([NH:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:22]1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 147292243-(Trityl-amino)-piperidin-2-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 21963705Piperidin-3-yl-trityl-amine収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Add 3-(trityl-amino)-piperidin-2-one (3.56 g, 10.0 mmol) in portions to a suspension of LiAlH4 (1.00 g, 26.5 mmol) in tetrahydrofuran (25 mL). Heat the reaction to reflux under nitrogen overnight. Cool the reaction to room temperature, add 1.0 mL water, follow by adding 3.0 mL 15% NaOH and 3.0 mL water. Filter the mixture, wash with tetrahydrofuran and concentrate. Patition the material between diethyl ether and water. Add 5.0N sodium hydroxide until the aqueous layer cleared. Extract he product from the aqueous layer with diethyl ether. Dry the combined organic layers over magnesium sulfate and concentrate to give 2.91 g of the title compound as a clear oil, 85% yield. 1H NMR: consistent with structure.

後処理

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux under nitrogen overnight
  4. temperatureCool
  5. customthe reaction to room temperature
  6. filtrationFilter the mixture
  7. washwash with tetrahydrofuran
  8. concentrationconcentrate
  9. additionAdd 5.0N sodium hydroxide until the aqueous layer
  10. extractionExtract he product from the aqueous layer with diethyl ether
  11. dry with materialDry the combined organic layers over magnesium sulfate
  12. concentrationconcentrate

出典と根拠

ORDレコード
ord-0c932675f6e94b0e97f9f0e362bb9e40
出典データセット
uspto-grants-2006_09
特許番号
US07101891B2

反応ノート

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