4-Cyclopropylaniline → 2,5-Bis(4-bromophenyl)-1-(4-cyclopropylphenyl)pyrrolidine

HRID 1470964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470964
CS(O[CH:6]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)(=O)=O.[CH:29]1([C:32]2[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=2)[CH2:31][CH2:30]1>CN(C=O)C>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[CH2:8][CH2:7][CH:6]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)[N:36]2[C:35]2[CH:37]=[CH:38][C:32]([CH:29]3[CH2:31][CH2:30]3)=[CH:33][CH:34]=2)=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 122539274-CyclopropylanilineHCID 582265311,4-Bis(4-bromophenyl)butane-1,4-diyl dimethanesulfonate

Produkt 1

HCID 672363922,5-Bis(4-bromophenyl)-1-(4-cyclopropylphenyl)pyrrolidineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The product from Example 42B (3.14 g, 5.64 mmol) and 4-cyclopropylaniline (6.01 g, 45.2 mmol) were combined in DMF (20 mL). The mixture was stirred at 50° C. under nitrogen for 3 hours. The reaction mixture was partitioned between 1M HCl and ethyl acetate. The organic layer was washed with brine three times, dried with sodium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane (0.5% to 1%) to give the title compound (2.12 g, 76%) as a mixture of stereoisomers as a sticky solid.

Aufarbeitung

  1. customThe reaction mixture was partitioned between 1M HCl and ethyl acetate
  2. washThe organic layer was washed with brine three times
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane (0.5% to 1%)

Quellen und Nachweise

ORD-Eintrag
ord-17d648c98f47420a9db69c33ebb5a368
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006387B2

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