Potassium Hydroxide → 7-[4-Nitro-3-(trifluoromethyl)phenyl]-7-azabicyclo[2.2.1]heptane

HRID 335392

Reaktionsgleichung

Reaktionsgleichung von HRID 335392
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[OH-].[K+].Cl.[CH:18]12[NH:24][CH:21]([CH2:22][CH2:23]1)[CH2:20][CH2:19]2>C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:24]2[CH:18]3[CH2:23][CH2:22][CH:21]2[CH2:20][CH2:19]3)=[CH:3][C:4]=1[C:11]([F:14])([F:13])[F:12])([O-:10])=[O:9]

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 162795037-Azabicyclo[2.2.1]heptane hydrochloride

Produkt 1

HCID 575168437-[4-Nitro-3-(trifluoromethyl)phenyl]-7-azabicyclo[2.2.1]heptane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-fluoro-1-nitro-2-(trifluoromethyl)benzene was dissolved in 3 vol DCM. Tetrabutylammoniumbromide (0.05 eq) and KOH (50 wt %, 3.6 eq) were added. 7-azabicyclo[2.2.1]heptane hydrochloride (8-HCl) was then added at 0-5° C. The reaction was warmed up to ambient temperature and monitored by HPLC. Once substantially complete, the layers were separated and the organic layer was washed with 1M HCl. The layers were separated and the aqueous layer was discarded. The organic layer was washed once with water, once with brine, and then distilled. The resulting material was recrystallized from cyclohexane at reflux. The solid was filtered, washed with cyclohexane, and dried in a vacuum oven at 45° C. with a N2 gas bleed to provide 7-[4-nitro-3-(trifluoromethyl)phenyl]-7-azabicyclo[2.2.1]heptane (9).

Aufarbeitung

  1. customOnce substantially complete, the layers were separated
  2. washthe organic layer was washed with 1M HCl
  3. customThe layers were separated
  4. washThe organic layer was washed once with water, once with brine
  5. distillationdistilled
  6. customThe resulting material was recrystallized from cyclohexane
  7. temperatureat reflux
  8. filtrationThe solid was filtered
  9. washwashed with cyclohexane
  10. dry with materialdried in a vacuum oven at 45° C. with a N2 gas

Quellen und Nachweise

ORD-Eintrag
ord-15aba32715384f66828f7e2d969d7239
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884018B2

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