Hydrochloric Acid → (2S)-1-methyl-5-oxopyrrolidine-2-carboxylic acid

HRID 554079Notes

Reaction equation

HRID 554079 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[CH2:9][CH2:8][C@H:3]1[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl>CO.O>[CH3:1][N:2]1[C:10](=[O:11])[CH2:9][CH2:8][C@H:3]1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12361160Methyl (2S)-1-methyl-5-oxoprolinate

Product 1

HCID 18649403(2S)-1-methyl-5-oxopyrrolidine-2-carboxylic acidYield 106.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 1-methyl-5-oxo-prolinate (0.308 g, 1.96 mmol) was dissolved in methanol (˜10 ml) and to this was added a solution of sodium hydroxide (0.157 g, 3.92 mmol) in water (˜10 ml). The mixture was heated at reflux for 3 hrs, then cooled and evaporated to leave a minimal amount of water. This was acidified to pH 1 using 2M aqueous hydrogen chloride. The aqueous layer was washed with dichloromethane and then separated and evaporated to give 1-methyl-5-oxo-proline as a white solid (0.300 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hrs
  3. temperaturecooled
  4. customevaporated
  5. customto leave a minimal amount of water
  6. washThe aqueous layer was washed with dichloromethane
  7. customseparated
  8. customevaporated

Sources & evidence

ORD record
ord-c0e5e7788bb447cab389b46f7b8ee996
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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