2-Chloroacetophenone → (3R)-1-(2-oxo-2-phenylethyl)-3-(2-(2-oxopyrrolidin-1-yl)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane chloride

HRID 404667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404667
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[O:11]=[C:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH:17]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:18]([O:20][C@@H:21]1[CH:26]2[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]2)[CH2:22]1)=[O:19]>CCOC(C)=O.C(#N)C>[Cl-:1].[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][N+:23]12[CH2:24][CH2:25][CH:26]([CH2:27][CH2:28]1)[C@@H:21]([O:20][C:18](=[O:19])[CH:17]([N:13]1[CH2:14][CH2:15][CH2:16][C:12]1=[O:11])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:22]2

Komponenten

5

Edukt 2

HCID 107572-ChloroacetophenoneHCID 86688927(R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate

Produkt 1

HCID 86688928(3R)-1-(2-oxo-2-phenylethyl)-3-(2-(2-oxopyrrolidin-1-yl)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane chlorideAusbeute 67,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Chloro-1-phenylethanone (62.1 mg, 0.40 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(2-oxopyrrolidin-1-yl)-2-phenylacetate (120 mg, 0.36 mmol) in EtOAc (2.4 ml) and acetonitrile (1.2 ml). The pale yellow solution was stirred at room temperature for three days. The solvent was evaporated and the crude was purified by flash chromatography (DCM/MeOH=9/1) to collect the title compound (118 mg, 66.9% yield) as an off-white spongy solid.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe crude was purified by flash chromatography (DCM/MeOH=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-6a8866aedb5848b7be26458da4bbc8f4
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748613B2

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