Water → 2-Hydroxy-2-(1-benzylpyrrolidin-3-yl)acetic acid

HRID 2050188Notes

Reaction equation

HRID 2050188 reaction equation
[OH:1][CH:2]([CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6]1)[C:3]#N.[OH-:17].[Na+].[OH2:19]>Cl>[OH:1][CH:2]([CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6]1)[C:3]([OH:19])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 203422572-Hydroxy-2-(1-benzylpyrrolidin-3-yl)acetonitrile

Product 1

HCID 203422522-Hydroxy-2-(1-benzylpyrrolidin-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 12.05 g of 2-hydroxy-2-(1-benzylpyrrolidin-3-yl)acetonitrile in 23 ml of concentrated hydrochloric acid is heated on a bath for 1 hour and allowed to stand overnight. After cooling, precipitated ammonium chloride is filtered off and washed with acetone. The combined filtrate and washings are evaporated under reduced pressure to yield the residue, which is dissolved in water, mixed with 20 ml of 23 (w/w) % aqueous sodium hydroxide solution and washed with methylene chloride. The aqueous layer is slowly adsorbed on a column of 300 ml of Amberlite IR-120B(H+) and after washing of the column with water, eluted with 1 N ammonium hydroxide. The eluate is evaporated to dryness under reduced pressure, and the residue is mixed with acetone. The precipitate, which appears, is collected by filtration and recrystallized from a mixture of ethanol and acetone to yield 1.422 g of 2-hydroxy-2-(1-benzylpyrrolidin-3-yl)acetic acid. mp. 174° to 176° C.

Workup

  1. temperatureAfter cooling
  2. customprecipitated ammonium chloride
  3. filtrationis filtered off
  4. washwashed with acetone
  5. customThe combined filtrate and washings are evaporated under reduced pressure
  6. customto yield the residue, which
  7. washwashed with methylene chloride
  8. washafter washing of the column with water
  9. washeluted with 1 N ammonium hydroxide
  10. customThe eluate is evaporated to dryness under reduced pressure
  11. additionthe residue is mixed with acetone
  12. filtrationis collected by filtration
  13. customrecrystallized from a mixture of ethanol and acetone

Sources & evidence

ORD record
ord-e2c219c51ff94af7b82d6b14fd481d4b
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Reaction notes

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