Methanol → [1-(3,5-Dimethoxyphenyl)pyrrolidin-2-yl]acetic acid

HRID 2073990Notes

Reaction equation

HRID 2073990 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[CH2:16][C:17]([O-:19])=[O:18])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CO.[OH-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[CH2:16][C:17]([OH:19])=[O:18])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86739683HCID 86739683, compound

Product 1

HCID 13366711[1-(3,5-Dimethoxyphenyl)pyrrolidin-2-yl]acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 53.6 g. (0.192 mole) methyl dl-2-[1-(3,5-dimethoxyphenyl)pyrrolidin-2-yl]acetate and 250 ml. methanol was warmed to obtain a solution and 22.8 g. (0.57 mole) sodium hydroxide in 200 ml. water was added. The resulting mixture was stirred at room temperature for 2.5 hours, the methanol evaporated and the aqueous residue cooled in ice. To this was added dropwise 48 ml. concentrated hydrochloric acid, the mixture extracted with 4x 150 ml. methylene chloride, the extract washed with water, dried (MgSO4) and the solvent evaporated to afford 48.9 g. (96%) of product. 1H-NMR (CDCl3) ppm (delta): 3.80 (s, 6H, OCH3), 4.10 (m, 1H, N--CH), 5.82 (s, 3H, aromatic), 11.0 (s, 1H, COOH). Mass spectrum (m/e): 206 (base peak), 265 (m+).

Workup

  1. additionA mixture of 53.6 g
  2. customto obtain a solution and 22.8 g
  3. customthe methanol evaporated
  4. temperaturethe aqueous residue cooled in ice
  5. additionTo this was added dropwise 48 ml
  6. extractionconcentrated hydrochloric acid, the mixture extracted with 4x 150 ml
  7. washmethylene chloride, the extract washed with water
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated
  10. customto afford 48.9 g

Sources & evidence

ORD record
ord-0ad617ffc3f5416e897327173eaf47ea
Source dataset
uspto-grants-1990_04
Patent number
US04920221

Reaction notes

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