Potassium Carbonate → cis-3-Benzyl-7-(2-fluoro-4-nitrophenyl)-3,7-diazabicyclo[3,3,0]octane

HRID 2288761노트

반응식

HRID 2288761 반응식
[CH2:1]([N:8]1[CH2:15][C@@H:14]2[C@@H:10]([CH2:11][NH:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1F.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]1[CH2:9][C@@H:10]2[C@@H:14]([CH2:13][N:12]([C:22]3[CH:21]=[CH:20][C:19]([N+:24]([O-:26])=[O:25])=[CH:18][C:17]=3[F:16])[CH2:11]2)[CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 1514450rel-(3aR,6aS)-Octahydro-2-(phenylmethyl)pyrrolo(3,4-c)pyrrole

생성물 1

HCID 21969626cis-3-Benzyl-7-(2-fluoro-4-nitrophenyl)-3,7-diazabicyclo[3,3,0]octane

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of cis-3-benzyl-3,7-diazabicyclo[3.3.0]octane (0.35 g, 1.73 mmol) in acetonitrile (10 mL) is added 3,4-difluoronitrobenzene (0. 19 mL, 1. 73 mmol) and potassium carbonate (0.60 g, 4.33 mmol) under a nitrogen atmosphere at ambient temperature. The reaction is stirred 15 hours, concentrated in vacuo, and diluted with ethyl acetate (100 mL). The organic phase is washed with water (3×20 mL) and saline (20 mL), dried over sodium sulfate, concentrated in vacuo, and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (99/1). The appropriate fractions are combined (Rf =0.49, TLC, chloroform/methanol, 95/5) and concentrated in vacuo to give the title compound, NMR (CDCl3) 7.94, 7.88, 7.29, 6.62, 3.73, 3.64, 3.44, 2.97, 2.75, 2.55.

후처리

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ethyl acetate (100 mL)
  3. washThe organic phase is washed with water (3×20 mL) and saline (20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel (230-400 mesh, 100 mL)
  7. washeluting with chloroform/methanol (99/1)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9138e89a8cad436ab9a5692c1d0ae950
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06090820

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