Water → Methyl 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoate

HRID 1930516ノート

反応式

HRID 1930516 の反応式
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2([C:28]([F:31])([F:30])[F:29])[CH2:27][CH2:26][NH:25][CH2:24]2)[CH:19]=[C:20]([Cl:22])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[Cl:22][C:20]1[CH:19]=[C:18]([C:23]2([C:28]([F:31])([F:30])[F:29])[CH2:27][CH2:26][N:25]([C:2]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=3)[CH2:24]2)[CH:17]=[C:16]([Cl:15])[CH:21]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14941412Methyl 4-fluoro-2-nitrobenzoateHCID 582188803-(3,5-Dichlorophenyl)-3-(trifluoromethyl)pyrrolidine

生成物 1

HCID 58218897Methyl 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoate収率 50.7%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

To the solution of methyl 4-fluoro-2-nitrobenzoate (1.1 g) and 3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidine (1.5 g) in 1-methyl-2-pyrrolidinone was added potassium carbonate (1.5 g) and the mixture was heated with stirring at 100° C. for two hours. The mixture was cooled to room temperature and then poured into water, which was then extracted twice with ethyl acetate. The organic layer was combined, which was then washed with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure, and the residue was then purified by silica gel chromatography to yield methyl 4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-nitrobenzoate (1.24 g). 1H-NMR (CDCl3) δ: 2.53-2.67 (1H, m), 2.89-2.97 (1H, m), 3.50-3.71 (2H, m), 3.83 (1H, d), 3.85 (3H, s), 4.15 (1H, d), 6.69 (1H, dd), 6.75 (1H, d), 7.26 (2H, d), 7.42 (1H, t), 7.81 (1H, d)

後処理

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. extractionwas then extracted twice with ethyl acetate
  4. washwhich was then washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter the drying agent was filtered off
  7. distillationthe solvent was distilled away under the reduced pressure
  8. customthe residue was then purified by silica gel chromatography

出典と根拠

ORDレコード
ord-9f53f8c84de2470383eefa5a8da667c3
出典データセット
uspto-grants-2012_05
特許番号
US08188122B2

反応ノート

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