Phenacyl bromide → (3R)-3-(2-(3-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 404671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404671
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Br:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]>C(#N)C>[Br-:26].[F:1][C:2]1[CH:3]=[C:4]([CH:8]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N+:14]([CH2:27][C:28](=[O:29])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6259Phenacyl bromideHCID 86688932(R)-quinuclidin-3-yl 2-(3-fluorophenyl)-2-(piperidin-1-yl)acetate

Produkt 1

HCID 86688933(3R)-3-(2-(3-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromideAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(R)-Quinuclidin-3-yl 2-(3-fluorophenyl)-2-(piperidin-1-yl)acetate (164 mg, 0.47 mmol) and 2-bromo-1-phenylethanone (104 mg, 0.52 mmol) were dissolved in acetonitrile (5 ml) and stirred at room temperature for 16 hours. The solvent was evaporated and the crude was triturated with Et2O, filtered under suction and washed with EtOAc and Et2O (1/1) to obtain (3R)-3-(2-(3-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (180.5 mg; 69.9% yield) as a white solid.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe crude was triturated with Et2O
  3. filtrationfiltered under suction
  4. washwashed with EtOAc and Et2O (1/1)

Quellen und Nachweise

ORD-Eintrag
ord-c00e6604ad494a0fbf685db8b986bb39
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748613B2

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