3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole → HCID 86688881, Verbindung

HRID 404620

Reaktionsgleichung

Reaktionsgleichung von HRID 404620
[C:1]1([CH:7]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]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.[Cl:25][CH2:26][C:27]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:29][N:28]=1>CCOC(C)=O.C(#N)C>[Cl-:25].[C:32]1([C:30]2[O:29][N:28]=[C:27]([CH2:26][N+:13]34[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]3)[C@@H:11]([O:10][C:8](=[O:9])[CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:12]4)[N:31]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Komponenten

5

Edukt 2

HCID 3021543-(Chloromethyl)-5-phenyl-1,2,4-oxadiazoleHCID 71603247(R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate

Produkt 1

HCID 86688881HCID 86688881, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(piperidin-1-yl)acetate (100 mg, 0.30 mmol) in EtOAc (2 ml) and acetonitrile (1 ml), was added 3-(chloromethyl)-5-phenyl-1,2,4-oxadiazole (71.1 mg, 0.36 mmol). The reaction was stirred at room temperature for 30 hours and then the solvents were evaporated. The residue was triturated with EtOAc (10 ml) and the solid was collected by suction filtration to obtain the title compound (113 mg, 71% yield) as a yellow solid.

Aufarbeitung

  1. customthe solvents were evaporated
  2. customThe residue was triturated with EtOAc (10 ml)
  3. filtrationthe solid was collected by suction filtration

Quellen und Nachweise

ORD-Eintrag
ord-cda9a5a040b84f9587363928bc0e3cde
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748613B2

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