Aluminium lithium hydride → (R)-2-((4-(3-(Difluoromethyl)-4-fluorophenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl)methyl)-1-methylpiperidine

HRID 1685173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685173
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:15]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]1[CH2:23][N:24]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([C:36](F)([F:38])[F:37])[CH:30]=2)[N:26]=[C:25]1[CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=O)C1C=CC=CC=1>C1COCC1>[F:38][CH:36]([F:37])[C:31]1[CH:30]=[C:29]([C:27]2[N:26]=[C:25]([CH:40]3[CH2:41][CH2:42][NH:43][CH2:44][CH2:45]3)[N:24]([CH2:23][C@H:18]3[CH2:19][CH2:20][CH2:21][CH2:22][N:17]3[CH3:15])[CH:28]=2)[CH:34]=[CH:33][C:32]=1[F:35]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 67264723(R)-benzyl-2-((4-(4-fluoro-3-(trifluoromethyl)phenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl)methyl)piperidine-1-carboxylate

Produkt 1

HCID 67265238(R)-2-((4-(3-(Difluoromethyl)-4-fluorophenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl)methyl)-1-methylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of Lithium aluminium hydride (0.638 g, 0.0168 mol, 5.0 eq) in 20 mL THF at 0° C., add (R)-benzyl-2-((4-(4-fluoro-3-(trifluoromethyl)phenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl)methyl)piperidine-1-carboxylate in small portions (2.2 g, 0.0033 mol, 1.0 eq). Stir the reaction at RT for 4 hours. After completion, cool the reaction and quench with ice cold water followed by 10% NaOH solution and stir at RT and filter the resulting suspension through Celite®, wash the solid cake with EA. Dry the filtrate over anhydrous sodium sulfate and concentrate under reduced pressure to get 1.6 g of the title compound. (ES+): m/z 407 (M+H).

Aufarbeitung

  1. customthe reaction at RT for 4 hours
  2. temperatureAfter completion, cool
  3. customthe reaction
  4. customquench with ice cold water
  5. stirringstir at RT
  6. filtrationfilter the resulting suspension through Celite®
  7. washwash the solid cake with EA
  8. dry with materialDry the filtrate over anhydrous sodium sulfate
  9. concentrationconcentrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-71867d76faa341ccab484ee20ecc3f65
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148387B2

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