Triethylamine → tert-butyl 4-(4-bromo-1-(2-((methylsulfonyl)oxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 2088891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2088891
[Br:1][C:2]1[N:3]=[C:4]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[N:5]([CH2:7][CH2:8][OH:9])[CH:6]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[Br:1][C:2]1[N:3]=[C:4]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[N:5]([CH2:7][CH2:8][O:9][S:31]([CH3:30])(=[O:33])=[O:32])[CH:6]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67265139tert-Butyl 4-(4-bromo-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Produkt 1

HCID 86641601tert-butyl 4-(4-bromo-1-(2-((methylsulfonyl)oxy)ethyl)-1H-imidazol-2-yl)piperidine-1-carboxylateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Combine tert-butyl 4-(4-bromo-1-(2-hydroxyethyl)-1H-imidazol-2-yl)piperidine-1-carboxylate (3.84 g, 10.26 mmol), dichloromethane (60 mL), and triethylamine (4.29 mL, 3.0 eq). Place under nitrogen and cool to 0° C. Add methanesulfonyl chloride (0.95 mL, 1.2 eq) dropwise. After 15 minutes, quench with saturated aqueous sodium bicarbonate. Wash the organics with saturated aqueous sodium chloride. Dry the organics over anhydrous magnesium sulfate, filter, and concentrate in vacuo to give the title compound (4.45 g, 96%). MS (ES) m/z=452 [M]+.

Aufarbeitung

  1. customquench with saturated aqueous sodium bicarbonate
  2. washWash the organics with saturated aqueous sodium chloride
  3. dry with materialDry the organics over anhydrous magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f0af52b84000475389a539afb57fe2ed
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436002B2

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