Diethyl Ether → (R)-3-((bis(3-fluorophenyl)methoxy)carbonylamino)-1-(2-(5-cyanothiophen-2-yl)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1910485Notes

Reaction equation

HRID 1910485 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[S:9][C:8]([C:10]#[N:11])=[CH:7][CH:6]=1)=[O:4].[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@@H:14]([NH:20][C:21](=[O:38])[O:22][CH:23]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=1)[CH2:13]2.CCOCC>C(OCC)(=O)C>[Br-:1].[F:37][C:33]1[CH:32]=[C:31]([CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[O:22][C:21]([NH:20][C@@H:14]2[CH:15]3[CH2:16][CH2:17][N+:12]([CH2:2][C:3]([C:5]4[S:9][C:8]([C:10]#[N:11])=[CH:7][CH:6]=4)=[O:4])([CH2:19][CH2:18]3)[CH2:13]2)=[O:38])[CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 112184615-(Bromoacetyl)thiophene-2-carbonitrile2×HCID 66575633(R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate

Product 1

HCID 86672920(R)-3-((bis(3-fluorophenyl)methoxy)carbonylamino)-1-(2-(5-cyanothiophen-2-yl)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 80.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-(2-Bromoacetyl)thiophene-2-carbonitrile (33.4 mg, 0.14 mmol) was added to a solution of (R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate (54 mg, 0.14 mmol, prepared as in example 1) in ethyl acetate (2 ml). The resulting solution was stirred at room temperature for two days, then 5-(2-bromoacetyl)thiophene-2-carbonitrile (3.4 mg, 0.015 mmol) was added, and the stirring was kept for additional 16 hours. Et2O was added and the precipitate was recovered by filtration to afford (R)-3-((bis(3-fluorophenyl)methoxy)carbonylamino)-1-(2-(5-cyanothiophen-2-yl)-2-oxoethyl)-1-azoniabicyclo[2.2.2]octane bromide (68 mg).

Workup

  1. waitthe stirring was kept for additional 16 hours
  2. filtrationthe precipitate was recovered by filtration

Sources & evidence

ORD record
ord-8bfc39ec053948c193187fba01378100
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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