Boron tribromide → 3-Cyclohexyl-1-(2,6-dichloro-4-hydroxy-benzyl)-pyrrolidin-2-one
Reaction equation
[CH:1]1([CH:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([O:20]C)=[CH:15][C:14]=3[Cl:22])[C:8]2=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>ClC(Cl)C>[CH:1]1([CH:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=3[Cl:22])[C:8]2=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Participants
4
Procedure
Treat a solution of 3-cyclohexyl-1-(2,6-dichloro-4-methoxy-benzyl)-pyrrolidin-2-one (1.3 g, 3.66 mmol) in dichloroethane (30 mL) at −20° C. with boron tribromide (1.0 M in DCM, 18.3 mL) for 2 hours. Warm the reaction up to room temperature and stir for 12 hours. Quench the reaction with methanol and remove the solvent under vacuum. Partition the residue with ethyl acetate and HCl (1 N). Wash the organic with water. After drying the organic layer, filtrate and concentrate to afford 1.2 g (99%) of the title compound. MS (m/z): 342 (M+).