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 469455Notes

Reaction equation

HRID 469455 reaction equation
[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

Participants

5

Reactant 3

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

Product 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 bromideYield 66.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  1. filtrationthe product was collected by suction filtration

Sources & evidence

ORD record
ord-e5a0008acff94f6fabe55240f9d4bae5
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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