Boron Trichloride → (3R)-1-Benzyl-3-Ethyl-7-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 898216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898216
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[N:11]([C:19](=[O:28])[C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=2)[C@H:10]([CH2:29][CH3:30])[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Cl)(Cl)Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[N:11]([C:19](=[O:28])[C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)[C@H:10]([CH2:29][CH3:30])[C:9]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 25135Boron TrichlorideHCID 69223935(3R)-1-benzyl-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Produkt 1

HCID 11682854(3R)-1-Benzyl-3-Ethyl-7-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-oneAusbeute 156,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of (3R)-1-benzyl-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (0.17 g, 0.41 mmol) and tetrabutylammonium iodide (0.28 g, 0.76 mmol) in methylene chloride (4 mL) at −78° C. was added a 1 M solution of boron trichloride in methylene chloride (2.8 mL, 2.8 mmol). Stirring was continued at −78° C. for 5 minutes, and the reaction was warmed to 0° C., where it was stirred for 10 h. Ice water was then added and stirred thoroughly. The layers were separated. The organic layer was washed with water and brine and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave an oil (0.26 g). The product was purified via Biotage Horizon® (SiO2, gradient from 5% EtOAc/hexane to 35% EtOAc/hexane) to quantitatively yield (3R)-1-benzyl-3-ethyl-7-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one as a colorless oil. [α]D25=250° (c=0.0097 G/ML, CHCl3); MS (ESI) m/z 405 ([M+H]+); MS (ESI) m/z 403 ([M−H]−); HRMS: calcd for C24H21FN2O3 0.67H2O, 416.2207; found (ESI+), 405.16006.

Aufarbeitung

  1. stirringwhere it was stirred for 10 h
  2. stirringstirred thoroughly
  3. customThe layers were separated
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fde716a8a0e340b982cfbbf23fa63d5a
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351709B2

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