Rolipram → 3-[4-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile

HRID 1727136

반응식

HRID 1727136 반응식
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][NH:18][C:17](=[O:20])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]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>CCOC(C)=O.[Cu]I.O1CCOCC1.CN(C=O)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][N:18]([C:22]4[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=4)[C:25]#[N:26])[C:17](=[O:20])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

9

반응물 4

HCID 5092RolipramHCID 233813-BromobenzonitrileHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, Tribasic

생성물 1

HCID 104746693-[4-(3-Cyclopentyloxy-4-methoxy-phenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile수율 96.2%

시약·촉매·용매 4

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

반응 조건

온도
110 °C

실험 절차

A mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one (1.5 g, 5 mmol), 3-bromobenzonitrile (1.36 g, 7.5 mmol), potassium phosphate (1.9 g, 9.8 mmol), and 1,2-trans-cyclohexanediamine (60 μL) was created in a dry round bottom flask under nitrogen containing DMF (9 mL) and dioxane (9 mL). The mixture was stirred and CuI (100 mg) was added. The resulting reaction mixture was heated to 110° C. with stirring under N2 for 20 h, and then cooled to r.t. The mixture was diluted with EtOAc and then filtered. The filtrate was washed with saturated aqueous solutions of NH4Cl and brine, dried over MgSO4, and concentrated under reduced pressure. Chromatography on silica gel (EtOAc:hexane=1:3 to 1:1) gave 1.81 g of 3-[4-(3-cyclopentyloxy-4-methoxy-phenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile. Yield: 90%.

후처리

  1. customwas created in a dry round bottom flask under nitrogen
  2. customThe resulting reaction mixture
  3. stirringwith stirring under N2 for 20 h
  4. temperaturecooled to r.t
  5. filtrationfiltered
  6. washThe filtrate was washed with saturated aqueous solutions of NH4Cl and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d126f3eed8c14591a419ca2157fcb205
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495016B2

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