Sulfuric Acid → 5-(2-Amino)ethyloxy-9-benzyl-7-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide

HRID 51340

反応式

HRID 51340 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.OS(O)(=O)=O.[CH2:17]([N:24]1[C:36]2[CH2:35][CH2:34][CH2:33][CH:32]([C:37]([NH2:39])=[O:38])[C:31]=2[C:30]2[C:25]1=[CH:26][C:27]([O:44][CH3:45])=[CH:28][C:29]=2[O:40][CH2:41][C:42]#[N:43])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[NH2:43][CH2:42][CH2:41][O:40][C:29]1[CH:28]=[C:27]([O:44][CH3:45])[CH:26]=[C:25]2[C:30]=1[C:31]1[CH:32]([C:37]([NH2:39])=[O:38])[CH2:33][CH2:34][CH2:35][C:36]=1[N:24]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 101349259-Benzyl-7-methoxy-5-cyanomethyloxy-1,2,3,4-tetrahydrocarbazole-4-carboxamideHCID 68718528lithium aluminium hydride THF

生成物 1

HCID 227391325-(2-Amino)ethyloxy-9-benzyl-7-methoxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide収率 55.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To 1.93 ml (1.93 mmol) 1M lithium aluminum hydride/THF in 13 ml THF at 0° C. was added H2SO4(53 μl, 0.97 mmol) dropwise over 5 min. The mixture was allowed to stir at room temperature 1 hour, then a solution of 9-benzyl-7-methoxy-5-cyanomethyloxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide (0.50 g, 1.29 mmol) in 13 ml THF was added dropwise at a rate which kept the temperature below 26° C. After an additional 45 minutes, the reaction was quenched with 0.5 ml 1:1 THF/H2O, 0.75 ml 13% NaOH, and finally 80 μl H2O. The reaction was diluted with EtOAc and saturated NaHCO3, and the layers separated. The organic layer was extracted with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 9:1:0.1 CH2Cl2/MeOH/NH4OH to give the subtitled product (0.28 g, 55%). MS (ES+) 394

後処理

  1. customthe temperature below 26° C
  2. waitAfter an additional 45 minutes
  3. customthe reaction was quenched with 0.5 ml 1:1 THF/H2O, 0.75 ml 13% NaOH, and finally 80 μl H2O
  4. additionThe reaction was diluted with EtOAc and saturated NaHCO3
  5. customthe layers separated
  6. extractionThe organic layer was extracted with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on silica gel eluting with 9:1:0.1 CH2Cl2/MeOH/NH4OH

出典と根拠

ORDレコード
ord-b3c0a4b14992469eaa6f497fccc83053
出典データセット
uspto-grants-2004_03
特許番号
US06713645B1

関連ノート

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