N-(1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-yl)benzamide → N-(1-(3-fluoro-4-hydroxyphenyl)-5-oxopyrrolidin-3-yl)benzamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8]C>B(Br)(Br)Br.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([NH:16][C:17](=[O:24])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:11]2)[CH:5]=[CH:6][C:7]=1[OH:8]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of N-(1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-yl)benzamide (Step 3, 0.9 g, 2.74 mmol) in 14 mL of 1 M BBr3/CH2Cl2 was stirred at RT for 16 h. The solution was concentrated in vacuo and the residue was diluted with 50 mL of MeOH and concentrated in vacuo again. The resulting yellow solid was washed with 50% EtOAc/hexane to give a yellow solid. MS (ESI pos. ion) m/z: 315.3 (M+H). Calc'd Exact Mass for C17H15FN2O3: 314.31.