Trifluoroacetic acid → 5-[(3,4-Dichlorophenyl)methyl]-2-azabicyclo[2.2.2]octane
Reaction equation
C(OC([N:8]1[CH2:13][CH:12]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]2[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)=O)(C)(C)C.ClCl.C(O)(C(F)(F)F)=O>>[Cl:24][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[Cl:23])[CH2:16][CH:11]1[CH2:10][CH:9]2[CH2:15][CH2:14][CH:12]1[CH2:13][NH:8]2Participants
4
Procedure
To a solution of 5-(3,4-dichloro-benzyl)-2-aza-bicyclo[2.2.2]octane-2-carboxylic acid tert-butyl ester (0.24 g, 0.65 mmol) in 2 mL of CH2 Cl2 was added 1 mL of TFA. After the mixture was stirred at rt for 1 h, it was quenched with NaHCO3 (sat.). It was then extracted with CH2Cl2 and the organic layer was washed with NaCl (sat.), dried over Na2SO4 and concentrated to give 170 mg of 5-(3,4-Dichloro-benzyl)-2-aza-bicyclo[2.2.2]octane (M++1: 270).