Water → 3-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]methyl}-5-methylbenzoic Acid

HRID 348938Notes

Reaction equation

HRID 348938 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[C:13]([O:15]C)=[O:14].O.[OH-].[Li+]>CO.O1CCCC1>[CH3:1][O:2][CH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[C:13]([OH:15])=[O:14]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57487367Methyl 3-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methyl}-5-methylbenzoate

Product 1

HCID 574873683-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]methyl}-5-methylbenzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]methyl}-5-methylbenzoate (170 mg, 0.50 mmol) in methanol (2 mL), tetrahydrofuran (1 mL), and water (1 mL) is added lithium hydroxide (211 mg, 5.0 mmol), and the reaction mixture stirred at room temperature for 2 h. The reaction mixture is concentrated under reduced pressure, dissolved in methylene chloride, filtered, and the filtrate concentrated under reduced pressure to provide the title compound. ESI MS m/z 264 [M+H]+.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutiondissolved in methylene chloride
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-75fc648c4e27401cb6eb0341c329b25c
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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