[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]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).
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