tert-butyl 4-[4-(3,6-dihydro-2H-pyran-4-yl)-1-(2-pyrrolidin-1-ylethyl)imidazol-2-yl]piperidine-1-carboxylate → HCID 67112170, Verbindung

HRID 2088922

Reaktionsgleichung

Reaktionsgleichung von HRID 2088922
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[N:8]=[C:9]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[N:10]([CH2:12][CH2:13][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:11]=2)[CH2:3][CH2:2]1>[Pd].C(O)C>[N:14]1([CH2:13][CH2:12][N:10]2[CH:11]=[C:7]([CH:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[N:8]=[C:9]2[CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

4

Edukt 1

HCID 67112253tert-butyl 4-[4-(3,6-dihydro-2H-pyran-4-yl)-1-(2-pyrrolidin-1-ylethyl)imidazol-2-yl]piperidine-1-carboxylate

Produkt 1

HCID 67112170HCID 67112170, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
67.5 °C

Versuchsvorschrift

Add palladium on charcoal, (3.0 g, 50% wet, 0.1 g/g limiting reagent) to a solution of tert-butyl 4-[4-(3,6-dihydro-2H-pyran-4-yl)-1-(2-pyrrolidin-1-ylethyl)imidazol-2-yl]piperidine-1-carboxylate (30 g, 69.67 mmol) in ethanol (210 mL). Stir under a hydrogen atmosphere in a Parr system (200 psi, 65-70° C.) for 27 hours. Add additional palladium on charcoal (0.6 g, 50% wet, 0.02 g/g limiting reagent) and stir under a hydrogen atmosphere in a Parr system (200 psi, 65-70° C.) for five hours. Filter over Celite® and wash with ethanol. Concentrate the filtrate in vacuo and dissolve the residue in ethanol (150 mL). Add palladium on charcoal (0.6 g, 50% wet, 0.02 g/g limiting reagent) and stir under a hydrogen atmosphere in a Parr system (250 psi, 70° C.) for 16 hours. Filter over Celite® and wash with ethanol. Concentrate the filtrate in vacuo to give tert-butyl 4-[1-(2-pyrrolidin-1-ylethyl)-4-tetrahydropyran-4-yl-imidazol-2-yl]piperidine-1-carboxylate as a brown oil (29.5 g, 98%). MS (ES) m/z=433 [M]+.

Aufarbeitung

  1. stirringstir under a hydrogen atmosphere in a Parr system (200 psi, 65-70° C.) for five hours
  2. filtrationFilter over Celite®
  3. washwash with ethanol
  4. concentrationConcentrate the filtrate in vacuo
  5. dissolutiondissolve the residue in ethanol (150 mL)
  6. stirringAdd palladium on charcoal (0.6 g, 50% wet, 0.02 g/g limiting reagent) and stir under a hydrogen atmosphere in a Parr system (250 psi, 70° C.) for 16 hours
  7. filtrationFilter over Celite®
  8. washwash with ethanol
  9. concentrationConcentrate the filtrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a0e551f8de2f4adba1e4ec9870e8f39b
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436002B2

Verknüpfte Notizen

Wird geladen…