4-Fluoroaniline → 1-(4-Fluorophenyl)-2,5-bis(4-nitrophenyl)pyrrolidine

HRID 2364773

Reaktionsgleichung

Reaktionsgleichung von HRID 2364773
CS(O[CH:6]([C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(=O)=O.[F:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1>>[F:33][C:34]1[CH:40]=[CH:39][C:37]([N:38]2[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[CH2:8][CH2:7][CH:6]2[C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)=[CH:36][CH:35]=1

Komponenten

3

Edukt 2

HCID 97314-FluoroanilineHCID 596171791,4-Bis(4-nitrophenyl)butane-1,4-diyl dimethanesulfonate

Produkt 1

HCID 596168701-(4-Fluorophenyl)-2,5-bis(4-nitrophenyl)pyrrolidineAusbeute 100 %

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The product from Example 1C (0.6 gm, 1.228 mmol) and 4-fluoroaniline (2.0 ml, 20.82 mmol) were combined and stirred at 50° C. overnight. The resulting mixture was partitioned between 0.2 N HCl (50 ml) and ethyl acetate (3×50 ml), and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel using a solvent gradient of 0-40% ethyl acetate in hexane to give the title compound as a mixture of cis and trans isomers (0.5 gm, 100% yield).

Aufarbeitung

  1. customThe resulting mixture was partitioned between 0.2 N HCl (50 ml) and ethyl acetate (3×50 ml)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography on silica gel using a solvent gradient of 0-40% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-9fa20f205f3b4ceb903779468fc2a327
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691938B2

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