2-(Chloroacetyl)thiophene → (R)-3-{2-[(4-fluoro-phenyl)-methyl-amino]-2-phenyl-acetoxy}-1-(2-oxo-2-thiophen-2-yl-ethyl)-1-azonia-bicyclo[2.2.2]octane chloride
Reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:27])[CH:11]([N:18]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH3:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2]2.[Cl:28][CH2:29][C:30]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=[O:31]>C(OCC)(=O)C>[Cl-:28].[F:26][C:23]1[CH:24]=[CH:25][C:20]([N:18]([CH3:19])[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]([O:9][C@@H:3]2[CH:4]3[CH2:7][CH2:8][N+:1]([CH2:29][C:30](=[O:31])[C:32]4[S:33][CH:34]=[CH:35][CH:36]=4)([CH2:6][CH2:5]3)[CH2:2]2)=[O:27])=[CH:21][CH:22]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of [(4-fluoro-phenyl)-methyl-amino]-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (C120) (100 mg, 0.27 mmol) in ethyl acetate (2.7 mL), is added 2-chloro-1-(thiophen-2-yl)ethanone (48.0 mg, 0.30 mmol). The reaction is stirred at RT for 3.5 days. The suspension is evaporated and the residue is triturated with Et2O (8 mL). The solid is filtered on a buckner funnel and the sticky solid is dissolved in DCM. The solution is evaporated giving the title compound as a pale yellow solid (120 mg, 84% yield, chloride salt, mixture of diastereoisomers).