Hydrochloric Acid → 1-(4-Fluorophenyl)-3-methyl-2-oxopyrrolidine-3-carboxylic acid

HRID 1676321Notes

Reaction equation

HRID 1676321 reaction equation
[Li+].[OH-].[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][C:12]([CH3:19])([C:15]([O:17]C)=[O:16])[C:11]2=[O:20])=[CH:6][CH:5]=1.Cl>C1COCC1.CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][C:12]([CH3:19])([C:15]([OH:17])=[O:16])[C:11]2=[O:20])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67348985Methyl 1-(4-fluorophenyl)-3-methyl-2-oxopyrrolidine-3-carboxylate

Product 1

HCID 673473951-(4-Fluorophenyl)-3-methyl-2-oxopyrrolidine-3-carboxylic acidYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (1.2 mL, 1.19 mmol, 1.0 M in H2O) was added to a solution of methyl 1-(4-fluorophenyl)-3-methyl-2-oxopyrrolidine-3-carboxylate (0.149 g, 0.593 mmol) in a mixture of THF (4.5 mL) and MeOH (1.5 mL) at room temperature for 1 hour. The reaction mixture was acidified with aq. 1 N HCl solution (1.4 mL), extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated to afford the desired product (0.13 g, 92%). 1H-NMR (400 MHz, CD3OD) δ 7.62 (m, 2H), 7.13 (t, 2H), 3.97 (m, 1H), 3.86 (m, 1H), 2.63 (m, 1H), 2.13 (m, 1H), 1.47 (s, 3H); 19F NMR (376 MHz, CD3OD) δ −119.3.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4311d485ff1d468e9843bbb49a0ac63b
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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