3-Bromobenzonitrile → 3-[4-(3-Benzyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile

HRID 1727148ノート

反応式

HRID 1727148 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:19][NH:18][C:17](=[O:20])[CH2:16]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[C:25]#[N:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C@@H]1(N)CCCC[C@H]1N>CN(C=O)C.O1CCOCC1.[Cu]I.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:19][N:18]([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[C:25]#[N:26])[C:17](=[O:20])[CH2:16]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

9

反応物 4

HCID 233813-BromobenzonitrileHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 688307524-[3-(Benzyloxy)phenyl]pyrrolidin-2-one

生成物 1

HCID 688298583-[4-(3-Benzyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile収率 55.1%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-(3-benzyloxyphenyl)-pyrrolidin-2-one (1.8 g, 6.7 mmol), 3-bromobenzonitrile (1.83 g, 1.5 eq) and potassium phosphate (2.6 g, 1.8 eq) was created in a dry flask with a stir bar under N2. This mixture was dissolved in 10 mL DMF and 10 mL dioxane. To this solution was added 60 μL of 1,2-trans-cyclohexanediamine and CuI (100 mg). The solution was stirred and heated at 100° C. under N2 for 20 h, and then cooled down to r.t. EtOAc (100 mL) was added and the mixture was filtered, washed with NH4Cl solution, water and brine. The solution was also dried over MgSO4 and concentrated under a reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc:Hexane=1:3) to give 1.36 g of the desired product. Yield: 55%.

後処理

  1. customwas created in a dry flask with a stir bar under N2
  2. temperaturecooled down to r.t
  3. filtrationthe mixture was filtered
  4. washwashed with NH4Cl solution, water and brine
  5. dry with materialThe solution was also dried over MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (EtOAc:Hexane=1:3)

出典と根拠

ORDレコード
ord-be3ae6e1ba01499bb62f8b527af4de23
出典データセット
uspto-grants-2009_02
特許番号
US07495016B2

反応ノート

読み込み中…