2-Butene, 1-bromo-3-methyl- → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(3-methylbut-2-enyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 469504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469504
[Br:1][CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5].[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([CH:15]([NH:27][C:28]2[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=2)[C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:16](=[O:26])[O:17][C@@H:18]2[CH:23]3[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]3)[CH2:19]2)=[CH:11][CH:10]=1>CCOC(C)=O>[Br-:1].[CH2:34]([O:33][C:31]([C:30]1[CH:29]=[C:28]([NH:27][CH:15]([C:12]2[CH:13]=[N:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)[C:16]([O:17][C@@H:18]2[CH:23]3[CH2:24][CH2:25][N+:20]([CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5])([CH2:21][CH2:22]3)[CH2:19]2)=[O:26])[CH:38]=[CH:37][CH:36]=1)=[O:32])[CH3:35]

Komponenten

4

Edukt 2

HCID 700922-Butene, 1-bromo-3-methyl-HCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

Produkt 1

HCID 67124898(3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(3-methylbut-2-enyl)-1-azoniabicyclo[2.2.2]octane bromideAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-Bromo-3-methylbut-2-ene (16.9 mg, 0.11 mmol) was added to a solution of ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (C65) (50 mg, 0.11 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was triturated with Et2O, filtered and dried. The product was purified by flash-chromatography (DCM/MeOH=97/3 to 9/1) to obtain (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(3-methylbut-2-enyl)-1-azoniabicyclo[2.2.2]octane bromide (56 mg, 84% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried
  5. customThe product was purified by flash-chromatography (DCM/MeOH=97/3 to 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-7f5d8f9f91ea4544ad1011ac3d5f8a6e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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