2-Bromo-1-(thiophen-2-yl)ethan-1-one → (3R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 469460Notes

Reaction equation

HRID 469460 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]([O:9][C@@H:10]2[CH:15]3[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]3)[CH2:11]2)=[O:8])[C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]1=2.[Br:29][CH2:30][C:31]([C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)=[O:32]>CCOC(C)=O>[Br-:29].[S:1]1[CH:5]=[C:4]([CH:6]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]([O:9][C@@H:10]2[CH:15]3[CH2:16][CH2:17][N+:12]([CH2:30][C:31](=[O:32])[C:33]4[S:34][CH:35]=[CH:36][CH:37]=4)([CH2:13][CH2:14]3)[CH2:11]2)=[O:8])[C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]1=2

Participants

4

Reactant 2

HCID 27763722-Bromo-1-(thiophen-2-yl)ethan-1-oneHCID 58556957(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate

Product 1

HCID 54765079(3R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 36.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate (C19) (90 mg, 0.23 mmol) was dissolved in EtOAc (3 ml), and 2-bromo-1-(thiophen-2-yl)ethanone (51.7 mg, 0.25 mmol) was added. The reaction mixture was stirred at room temperature overnight. The crude was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (50 mg, 36.5% yield).

Workup

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

Sources & evidence

ORD record
ord-2a993f0564b44601ac1b8708e2b87f6d
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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