Lithium Hydroxide → 2-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

HRID 2408841Notes

Reaction equation

HRID 2408841 reaction equation
[O:1]=[C:2]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([O:22]CC)=[O:21].[OH-].[Li+]>C(O)C.O>[O:1]=[C:2]1[C:6]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][N:3]1[CH2:19][C:20]([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67359197Ethyl 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetate

Product 1

HCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The product from Example 21B (0.92 g, 2.84 mmol) was dissolved in ethanol (20 mL). A solution of lithium hydroxide (0.57 g, 23.8 mmol) in water (5 mL) was added, and the reaction was heated to 80° C. for 2 hours. The reaction mixture was cooled to room temperature, concentrated, neutralized with 2 N HCl, and then diluted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and then concentrated to give the title compound. MS (DCI+) m/z 296.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4a4fbfcd38104bb08b98e38b2ea3432f
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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