Phosphoric Acid → tert-butyl 4-(4-ethyl-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 2088938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2088938
O[CH:2]([C:4]1[N:5]=[C:6]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[N:7]([CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=1)[CH3:3].P(=O)(O)(O)O>CO.[OH-].[OH-].[Pd+2]>[CH2:2]([C:4]1[N:5]=[C:6]([CH:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:20][CH2:21]2)[N:7]([CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:8]=1)[CH3:3]

Komponenten

5

Edukt 2

HCID 1004Phosphoric AcidHCID 67955049tert-butyl 4-(4-(1-hydroxyethyl)-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Produkt 1

HCID 67954430tert-butyl 4-(4-ethyl-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Add palladium hydroxide on carbon (4.20 g, 60% wet, 0.15 g/g limiting reagent) to a solution of tert-butyl 4-(4-(1-hydroxyethyl)-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate; phosphoric acid (28.00 g, 57.08 mmol) in methanol (10 mL). Stir under a hydrogen atmosphere in a Parr system (150 psi, 60° C.) for six days. Stir further under a hydrogen atmosphere in a Parr system (300 psi, 80° C.) for seven days. Filter over Celite®. Concentrate the filtrate in vacuo and dilute with acetone (280 mL). Stir overnight at room temperature. Filter and dry the resulting white solid under vacuum to give tert-butyl 4-(4-ethyl-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate; phosphoric acid (23.00 g, 85%). MS (ES) m/z=377 [M]+.

Aufarbeitung

  1. stirringStir further under a hydrogen atmosphere in a Parr system (300 psi, 80° C.) for seven days
  2. filtrationFilter over Celite®
  3. concentrationConcentrate the filtrate in vacuo
  4. additiondilute with acetone (280 mL)
  5. stirringStir overnight at room temperature
  6. filtrationFilter
  7. customdry the resulting white solid under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-82ef9fc9be4c4134a0c5724e75fd4e39
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436002B2

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