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

HRID 335392

反応式

HRID 335392 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-15aba32715384f66828f7e2d969d7239
出典データセット
uspto-grants-2014_11
特許番号
US08884018B2

関連ノート

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