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Acetic Acid → 4-Methyl-7-{1-(tert-butoxycarbonyl)-5-[(2-hydroxyethylamino)methyl]indol-2-yl}isoindolinone

HRID 21219
ノート
印刷プレビュー

反応式

HRID 21219 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].[CH2:30]([CH2:32][NH2:33])[OH:31].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(#N)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:33][CH2:32][CH2:30][OH:31])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 700EthanolamineHCID 5049666Sodium triacetoxyborohydrideHCID 866282884-Methyl-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

生成物 1

HCID 684919014-Methyl-7-{1-(tert-butoxycarbonyl)-5-[(2-hydroxyethylamino)methyl]indol-2-yl}isoindolinone
収率 81%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

In a similar manner to Step 2 of Example 6, 4-methyl-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (54.0 mg, 0.138 mmol) was dissolved in acetonitrile (4.3 mL), and the solution was treated with ethanolamine (0.034 mL, 0.55 mmol), acetic acid (0.158 mL, 2.76 mmol) and sodium triacetoxyborohydride (58.0 mg, 0.276 mmol). The reaction mixture was added with 1 mol/L hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with sodium carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-methyl-7-{1-(tert-butoxycarbonyl)-5-[(2-hydroxyethylamino)methyl]indol-2-yl}isoindolinone (48.5 mg, yield 81%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with sodium carbonate and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-583bf1d0b8674b22a2c5c8f36722450e
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07745641B2

反応ノート

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