2-(Chloroacetyl)thiophene → 3-(((3,4-Difluorophenyl)(phenyl)methoxy)carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 1910512Notes

Reaction equation

HRID 1910512 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH2:2]2.[Cl:27][CH2:28][C:29]([C:31]1[S:32][CH:33]=[CH:34][CH:35]=1)=[O:30]>C(OCC)(=O)C>[Cl-:27].[F:26][C:21]1[CH:20]=[C:19]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:11][C:9]([CH:3]2[CH:4]3[CH2:5][CH2:6][N+:1]([CH2:28][C:29](=[O:30])[C:31]4[S:32][CH:33]=[CH:34][CH:35]=4)([CH2:8][CH2:7]3)[CH2:2]2)=[O:10])[CH:24]=[CH:23][C:22]=1[F:25]

Participants

4

Reactant 2

HCID 27579252-(Chloroacetyl)thiopheneHCID 70925855(3,4-Difluorophenyl)(phenyl)methyl quinuclidine-3-carboxylate

Product 1

HCID 866729463-(((3,4-Difluorophenyl)(phenyl)methoxy)carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chlorideYield 21.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3,4-difluorophenyl)(phenyl)methyl quinuclidine-3-carboxylate (65 mg, 0.18 mmol) in ethyl acetate (3 ml), 2-chloro-1-(thiophen-2-yl)ethanone (29.2 mg, 0.18 mmol) was added, and the mixture was stirred at room temperature overnight. The solvent was removed under vacuum, and the residue was taken up with diethyl ether and filtered to give 3-(((3,4-difluorophenyl)(phenyl)methoxy)carbonyl)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (20 mg, mixture of diastereoisomers).

Workup

  1. customThe solvent was removed under vacuum
  2. filtrationfiltered

Sources & evidence

ORD record
ord-f77115a89afd40a8afc2ba17a3e8edac
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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