Diethyl Ether → (3R)-3-(2-(4-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 404685Notes

Reaction equation

HRID 404685 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])=[CH:13][CH:12]=1.CCOCC>CCOC(C)=O>[Cl-:1].[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N+:23]([CH2:2][C:3](=[O:4])[C:5]4[S:6][CH:7]=[CH:8][CH:9]=4)([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27579252-(Chloroacetyl)thiopheneHCID 86688942(R)-quinuclidin-3-yl 2-(4-fluorophenyl)-2-(piperidin-1-yl)acetate

Product 1

HCID 86688945(3R)-3-(2-(4-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chlorideYield 26.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-(thiophen-2-yl)ethanone (30.6 mg, 0.19 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(4-fluorophenyl)-2-(piperidin-1-yl)acetate (60 mg, 0.17 mmol) in EtOAc (3 ml). The reaction was stirred at room temperature for 16 hours. Et2O was added the precipitate was collected by filtration and purified by flash chromatography (DCM/MeOH/NH4OH=97/3/0.3) to obtain (3R)-3-(2-(4-fluorophenyl)-2-(piperidin-1-yl)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (23 mg, 26.2% yield) as a white solid.

Workup

  1. filtrationwas collected by filtration
  2. custompurified by flash chromatography (DCM/MeOH/NH4OH=97/3/0.3)

Sources & evidence

ORD record
ord-6318319131db4fd8a7736c6a7ee31437
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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