Methanol → 4-[1-(4-Fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid

HRID 889039Notes

Reaction equation

HRID 889039 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]2[CH2:16][C:15](=[O:17])[N:14]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:13]2)=[CH:6][CH:5]=1.CO.O.O[Li].O>C1COCC1>[F:24][C:21]1[CH:20]=[CH:19][C:18]([N:14]2[C:15](=[O:17])[CH2:16][CH:12]([CH2:11][O:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[CH:5][CH:6]=3)[CH2:13]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 117249774-[1-(4-Fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid methyl ester

Product 1

HCID 104717594-[1-(4-Fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acidYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-[1-(4-fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid methyl ester obtained in step 1 (0.14 g, 0.408 mmol) in THF:MeOH:H2O (6 mL, 2:1:3), LiOH.H2O was added at 20-25° C. The reaction mixture was stirred for 16 hours at that temperature. The solvents were removed under reduced pressure and the residue was diluted with water (10 ml). The aqueous layer was washed with DCM, acidified with 2% HCl. The acidified mixture was extracted with ethyl acetate, washed with brine, dried over Na2SO4. The organic layer was evaporated under reduced pressure to obtain 4-[1-(4-fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid (0.130 g, quantitative) as a white solid.

Workup

  1. customThe solvents were removed under reduced pressure
  2. additionthe residue was diluted with water (10 ml)
  3. washThe aqueous layer was washed with DCM
  4. extractionThe acidified mixture was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe organic layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-91a2a5b82f5f4a838bd20c00f1b9b1f3
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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