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

HRID 1819348노트

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HRID 1819348 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-65d19433d32e41f382eda52b3079dbb2
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601742B2

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