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

HRID 1162937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162937
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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 231567927-(2-hydroxyethylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneAusbeute 112,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6b705908f65145929fe4c45b7bb3090a
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820693B2

Notizen zur Reaktion

Wird geladen…