Benzene, (3-bromopropoxy)- → (3R)-3-(2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 469457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 469457
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[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>CCOC(C)=O>[Br-:1].[CH3:30][O:29][C:27]([C:23]1[S:24][CH:25]=[CH:26][C:22]=1[NH:21][CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:13]([O:31][C@@H:32]1[CH:37]2[CH2:36][CH2:35][N+:34]([CH2:2][CH2:3][CH2:4][O:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)([CH2:39][CH2:38]2)[CH2:33]1)=[O:12])=[O:28]

Komponenten

4

Edukt 2

HCID 68522Benzene, (3-bromopropoxy)-HCID 46840422HCID 46840422, Verbindung

Produkt 1

HCID 54765075(3R)-3-(2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromideAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(3-Bromopropoxy)benzene (19.7 μl, 0.12 mmol) was added to a solution of methyl 3-(2-oxo-1-phenyl-2-((R)-quinuclidin-3-yloxy)ethylamino)thiophene-2-carboxylate (C11) (50 mg, 0.12 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was triturated with Et2O and then purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide (25.3 mg, 32.9% yield).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. custompurified by preparative HPLC (Eluent: CH3CN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-dde95ab927814fe7a88e2f3f0f67aeaa
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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