Tetrahydrofuran → 7-(2-hydroxyethylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162937ノート

反応式

HRID 1162937 の反応式
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.[Si]([O:31][CH2:32][CH2:33][NH:34][C:35]1[CH:44]=[C:43]2[C:38]([CH:39]=[C:40]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[C:52]([F:55])([F:54])[F:53])[NH:41][C:42]2=[O:45])=[CH:37][CH:36]=1)(C(C)(C)C)(C)C.[Cl-].[NH4+]>C(OCC)(=O)C>[OH:31][CH2:32][CH2:33][NH:34][C:35]1[CH:44]=[C:43]2[C:38]([CH:39]=[C:40]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[C:52]([F:55])([F:53])[F:54])[NH:41][C:42]2=[O:45])=[CH:37][CH:36]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 575581107-[2-(tert-butyldimethylsilanyloxy)ethylamino]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

生成物 1

HCID 231567927-(2-hydroxyethylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one収率 112.6%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

TBAF (1 M THF solution, 88.2 μL, 0.882 mmol) was added to a THF solution (4 mL) that contained the 7-[2-(tert-butyldimethylsilanyloxy)ethylamino]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (204 mg, 0.441 mmol) obtained in step A, and the obtained mixture was then stirred at a room temperature for 1 hour. Thereafter, the reaction solution was poured into a mixed solution of ethyl acetate and a saturated ammonium chloride aqueous solution. An organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1 to 10:1), so as to obtain 7-(2-hydroxyethylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (173 mg, quant).

後処理

  1. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  2. distillationthe solvent was then distilled away under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=40:1 to 10:1)

出典と根拠

ORDレコード
ord-6b705908f65145929fe4c45b7bb3090a
出典データセット
uspto-grants-2010_10
特許番号
US07820693B2

反応ノート

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