Diethyl Ether → (R)-3-((bis(3-fluorophenyl)methoxy)-carbonylamino)-1-(2-oxo-2-(thiophen-3-yl)ethyl)-1-azoniabicyclo[2.2.2]-octane bromide

HRID 1910484Notes

Reaction equation

HRID 1910484 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)=[O:4].[N:10]12[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]1)[C@@H:12]([NH:18][C:19](=[O:36])[O:20][CH:21]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=1)[CH2:11]2.CCOCC>C(OCC)(=O)C>[Br-:1].[F:35][C:31]1[CH:30]=[C:29]([CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[O:20][C:19]([NH:18][C@@H:12]2[CH:13]3[CH2:14][CH2:15][N+:10]([CH2:2][C:3](=[O:4])[C:5]4[CH:9]=[CH:8][S:7][CH:6]=4)([CH2:17][CH2:16]3)[CH2:11]2)=[O:36])[CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-oneHCID 66575633(R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate

Product 1

HCID 70675261(R)-3-((bis(3-fluorophenyl)methoxy)-carbonylamino)-1-(2-oxo-2-(thiophen-3-yl)ethyl)-1-azoniabicyclo[2.2.2]-octane bromideYield 88.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(thiophen-3-yl)ethanone (27.5 mg, 0.13 mmol) was added to a solution of (R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate (50 mg, 0.13 mmol, prepared as in example 1) in ethyl acetate (2 ml). The reaction was stirred at room temperature overnight. Et2O (2 ml) was added, and the precipitate was collected by suction filtration and dried under vacuum at 40° C. over a week-end to obtain (R)-3-((bis(3-fluorophenyl)methoxy)-carbonylamino)-1-(2-oxo-2-(thiophen-3-yl)ethyl)-1-azoniabicyclo[2.2.2]-octane bromide (66.3 mg).

Workup

  1. filtrationthe precipitate was collected by suction filtration
  2. customdried under vacuum at 40° C. over a week-end

Sources & evidence

ORD record
ord-6e7d326994144160b278cbfa2f491d3f
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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