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

HRID 83826

반응식

HRID 83826 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9e5f55bc6f7d4143ae246fbcfb38ecfb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846739B2

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