Ammonium fluoride → (1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine

HRID 323510

反応式

HRID 323510 の反応式
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[NH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]1)(C(C)(C)C)(C)C.[F-].[NH4+].C(=O)(O)[O-].[Na+]>CO>[OH:8][CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[NH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:22]1

参加物

5

反応物 3

HCID 25516Ammonium fluorideHCID 516892Sodium BicarbonateHCID 22009292(1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine

生成物 1

HCID 22009172(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

Combine (1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine (0.53 g, 12 mmol) and ammonium fluoride (2.667 g, 72 mmol) in methanol (60 mL). Heat to about 60° C. After 2.5 hours, cool, evaporate in vacuo and partition the evaporated reaction mixture between dichloromethane and a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the organic layer twice with water and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give (1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine.

後処理

  1. temperaturecool
  2. customevaporate in vacuo
  3. custompartition
  4. customthe evaporated reaction mixture between dichloromethane
  5. customSeparate the layers
  6. extractionextract the organic layer twice with water
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo

出典と根拠

ORDレコード
ord-442278bd30b547888e969a8de56d3b47
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

関連ノート

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