Aluminium lithium hydride → 3,3-Bis(4-fluorophenyl)pyrrolidine

HRID 1667239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667239
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][C:9]2=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 673585653,3-Bis(4-fluorophenyl)pyrrolidin-2-one

Produkt 1

HCID 673601783,3-Bis(4-fluorophenyl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

In a 500 mL flask containing 3,3-bis(4-fluorophenyl)pyrrolidin-2-one (Example 58B, 4.1 g, 15 mmol) as a suspension in ether (300 mL) was added lithium aluminum hydride (2.0 Min tetrahydrofuran, 15 mL, 30 mmol) slowly via syringe under nitrogen. The reaction was refluxed overnight, cooled to room temperature, and then carefully quenched by the slow addition of 1 N NaOH (60 mL). The reaction was diluted with ethyl acetate (200 mL) and filtered through a pad of diatomaceous earth. The organic phase was separated, concentrated, and the residue purified over silica gel eluting with 97:3 dichloromethane/methanol to give the title compound. MS (DCI+) m/z 260 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction was refluxed overnight
  2. customcarefully quenched by the slow addition of 1 N NaOH (60 mL)
  3. additionThe reaction was diluted with ethyl acetate (200 mL)
  4. filtrationfiltered through a pad of diatomaceous earth
  5. customThe organic phase was separated
  6. concentrationconcentrated
  7. customthe residue purified over silica gel eluting with 97:3 dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-dc536e9d329b443cb9082355524e3ceb
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044069B2

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