Diethyl Ether → (R)-1-(2-oxo-2-phenyl-ethyl)-3-((R)-2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 1255063

Reaktionsgleichung

Reaktionsgleichung von HRID 1255063
[C:1]1([CH:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29].CCOCC>CCOC(C)=O>[Br-:26].[O:29]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:27][N+:13]12[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]1)[C@@H:11]([O:10][C:8](=[O:9])[C@@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12]2

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 6259Phenacyl bromideHCID 46239457(R)-quinuclidin-3-yl 2-phenyl-2-(phenylamino)acetate

Produkt 1

HCID 46841520(R)-1-(2-oxo-2-phenyl-ethyl)-3-((R)-2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(R)-quinuclidin-3-yl 2-phenyl-2-(phenylamino)acetate (Diasteroisomer 1 of C2) (20.3 mg, 0.06 mmol) is dissolved in EtOAc (0.60 mL) and 2-bromo-1-phenylethanone (12.0 mg, 0.06 mmol) is added. The reaction is stirred at room temperature for 2 hours (UPLC-MS: complete and clean conversion). Et2O (0.20 mL) were added and the product is triturated to obtain a white solid which is isolated by filtration and dried under vacuum overnight (31 mg, 96% yield, bromide salt, single diastereoisomer).

Aufarbeitung

  1. customthe product is triturated
  2. customto obtain a white solid which
  3. customis isolated by filtration
  4. dry with materialdried under vacuum overnight (31 mg, 96% yield, bromide salt, single diastereoisomer)

Quellen und Nachweise

ORD-Eintrag
ord-6f8a4ac877bb4644a4ebc62c56c904fe
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455646B2

Verknüpfte Notizen

Wird geladen…