Dabco → 1-(2-(Tert-butoxycarbonylamino)ethyl)-4-aza-1-azonia-bicyclo[2.2.2]octane bromide

HRID 83826

Reaktionsgleichung

Reaktionsgleichung von HRID 83826
[N:1]12[CH2:8][CH2:7][N:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Br:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]>CCOCC>[Br-:9].[C:15]([O:14][C:13]([NH:12][CH2:11][CH2:10][N+:1]12[CH2:8][CH2:7][N:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2)=[O:19])([CH3:18])([CH3:17])[CH3:16]

Komponenten

4

Edukt 2

HCID 9237DabcoHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Produkt 1

HCID 672353081-(2-(Tert-butoxycarbonylamino)ethyl)-4-aza-1-azonia-bicyclo[2.2.2]octane bromideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 1,4-diazabicyclo[2.2.2]octane (0.40 g, 3.57 mmol) in ether (5 mL) was added tert-butyl 2-bromoethylcarbamate (0.80 g, 3.57 mmol). The reaction was stirred overnight and the solvent was removed in vacuo. EtOAc (10 mL) was added and the reaction was stirred vigorously overnight. The precipitates were collected by filtration to give 1-(2-(tert-butoxycarbonylamino)ethyl)-4-aza-1-azonia-bicyclo[2.2.2]octane bromide (0.84 g) as a white solid. The solids were dissolved in MeOH (3 mL) and 4 M HCl in dioxane (3.5 mL, 14 mmol). The reaction was stirred at room temperature until it was determined to be complete by LCMS. The mixture was filtered to afford 1-(2-aminoethyl)-4-aza-1-azoniabicyclo[2.2.2]octane chloride hydrochloride (0.74 g) as a white solid. 1H-NMR (D2O, 400 MHz) δ 3.98-3.72 (m, 8H), 3.79-3.69 (m, 6H), 3.66-3.61 (m, 2H).

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. additionEtOAc (10 mL) was added
  3. stirringthe reaction was stirred vigorously overnight
  4. filtrationThe precipitates were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-9e5f55bc6f7d4143ae246fbcfb38ecfb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846739B2

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