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

HRID 898216ノート

反応式

HRID 898216 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 11682854(3R)-1-Benzyl-3-Ethyl-7-fluoro-4-(4-hydroxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one収率 156.8%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fde716a8a0e340b982cfbbf23fa63d5a
出典データセット
uspto-grants-2008_04
特許番号
US07351709B2

反応ノート

読み込み中…