Diethyl Ether → (3R)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-3-(2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 469455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469455
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4].[O:12]=[C:13]([O:31][C@@H:32]1[CH:37]2[CH2:38][CH2:39][N:34]([CH2:35][CH2:36]2)[CH2:33]1)[CH:14]([NH:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[C:27]([O:29][CH3:30])=[O:28])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCOCC>C(#N)C>[Br-:1].[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N+:34]23[CH2:39][CH2:38][CH:37]([CH2:36][CH2:35]2)[C@@H:32]([O:31][C:13](=[O:12])[CH:14]([NH:21][C:22]2[CH:26]=[CH:25][S:24][C:23]=2[C:27]([O:29][CH3:30])=[O:28])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:33]3)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 46840422HCID 46840422, Verbindung

Produkt 1

HCID 86660322(3R)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-3-(2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane bromideAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Bromo-1-(4-hydroxyphenyl)ethanone (19.9 mg, 0.09 mmol) was added to a solution of methyl 3-(2-oxo-1-phenyl-2-((R)-quinuclidin-3-yloxy)ethylamino)thiophene-2-carboxylate (C11) (37 mg, 0.09 mmol) in acetonitrile (2 ml). The reaction mixture was stirred at room temperature overnight, and then Et2O (1 ml) was added and the product was collected by suction filtration to obtain (3R)-1-(2-(4-hydroxyphenyl)-2-oxoethyl)-3-(2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetoxy)-1-azoniabicyclo[2.2.2]octane bromide (36.7 mg, 64.5% yield).

Aufarbeitung

  1. filtrationthe product was collected by suction filtration

Quellen und Nachweise

ORD-Eintrag
ord-e5a0008acff94f6fabe55240f9d4bae5
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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