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

HRID 482999Notes

Reaction equation

HRID 482999 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, 250 ml. methanol and 22.8 g. (0.57 mole) sodium hydroxide in 200 ml. water was stirred at room temperature for 2.5 hours. The methanol was evaporated and the aqueous residue cooled in ice. To this was added dropwise 48 ml. concentrated hydrochloric acid, the mixture extracted with 4×150 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. customThe methanol was evaporated
  3. temperaturethe aqueous residue cooled in ice
  4. additionTo this was added dropwise 48 ml
  5. extractionconcentrated hydrochloric acid, the mixture extracted with 4×150 ml
  6. washmethylene chloride, the extract washed with water
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated
  9. customto afford 48.9 g

Sources & evidence

ORD record
ord-368cf32567574e78a9390b27d7c1a6a0
Source dataset
uspto-grants-1986_03
Patent number
US04576964

Reaction notes

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