Potassium Carbonate → cis-3-Benzyl-7-(2-fluoro-4-nitrophenyl)-3,7-diazabicyclo[3,3,0]octane
Reaction equation
[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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- concentrationconcentrated in vacuo
- additiondiluted with ethyl acetate (100 mL)
- washThe organic phase is washed with water (3×20 mL) and saline (20 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customchromatographed on silica gel (230-400 mesh, 100 mL)
- washeluting with chloroform/methanol (99/1)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-9138e89a8cad436ab9a5692c1d0ae950
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06090820
Reaction notes
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