Diethyl Ether → (R)-1-[(3-Fluoro-phenylcarbamoyl)-methyl]-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2192315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192315
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Br:24][CH2:25][C:26]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=1)=[O:27].C(OCC)C.CCCC(C)C>C(#N)C>[Br-:24].[F:35][C:31]1[CH:30]=[C:29]([NH:28][C:26]([CH2:25][N+:1]23[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:27])[CH:34]=[CH:33][CH:32]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 78922-MethylpentaneHCID 34164032-bromo-N-(3-fluorophenyl)acetamideHCID 58348375HCID 58348375, Verbindung

Produkt 1

HCID 86655273(R)-1-[(3-Fluoro-phenylcarbamoyl)-methyl]-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromideAusbeute 55,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Thiophen-2-yl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 5d) (96 mg) and 2-bromo-N-(3-fluoro-phenyl)-acetamide (Example 8a) (67 mg) were dissolved in acetonitrile (2 mL) and left overnight. Diethyl ether (10 mL) and isohexane (8 mL) were added and the mixture was left overnight. The resulting crystals were filtered off and washed with diethyl ether to afford the titled compound (90 mg).

Aufarbeitung

  1. waitthe mixture was left overnight
  2. filtrationThe resulting crystals were filtered off
  3. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-479bf25aeb0444b48ae82b3c66877e74
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329729B2

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