Dimethylformamide → tert-Butyl 4-(4-bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 2088893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2088893
[Br:1][C:2]1[N:3]=[C:4]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[N:5]([CH2:7][CH2:8]OS(C)(=O)=O)[CH:6]=1.CN(C)C=O.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[N:5]([CH2:7][CH2:8][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:6]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 86641601tert-butyl 4-(4-bromo-1-(2-((methylsulfonyl)oxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Produkt 1

HCID 67112012tert-Butyl 4-(4-bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Combine tert-butyl 4-(4-bromo-1-(2-(methylsulfonyloxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (4.45 g, 9.84 mmol), dimethylformamide (25 mL), and pyrrolidine (2.46 mL, 3.0 eq) under nitrogen. Heat the reaction mixture at 50° C. overnight, then allow to cool to room temperature. Dilute with ethyl acetate. Wash with water followed by saturated aqueous sodium chloride. Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo to give the title compound (4.12 g, 98%). MS (ES) m/z=427 [M]+.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washWash with water
  3. dry with materialDry the organics over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b3617d0d3c8444f2ae099d59c7f54279
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436002B2

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