N-(1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-yl)benzamide → N-(1-(3-fluoro-4-hydroxyphenyl)-5-oxopyrrolidin-3-yl)benzamide

HRID 1993382Notes

Reaction equation

HRID 1993382 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

HCID 68419077N-(1-(3-fluoro-4-methoxyphenyl)-5-oxopyrrolidin-3-yl)benzamide

Product 1

HCID 68421403N-(1-(3-fluoro-4-hydroxyphenyl)-5-oxopyrrolidin-3-yl)benzamide

Reagents, catalysts & solvents 1

HCID 22277759Boron tribromide dichloromethaneSolvent

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.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionthe residue was diluted with 50 mL of MeOH
  3. concentrationconcentrated in vacuo again
  4. washThe resulting yellow solid was washed with 50% EtOAc/hexane
  5. customto give a yellow solid

Sources & evidence

ORD record
ord-5ea649c3993d4a92ab11735c8c9353eb
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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