Sodium Hydroxide → (2S)-1-methyl-5-oxopyrrolidine-2-carboxylic acid

HRID 2238518

Reaction equation

HRID 2238518 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[CH2:10][CH2:9][C@H:3]1[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[C:11](=[O:12])[CH2:10][CH2:9][C@H:3]1[C:4]([OH:6])=[O:5]

Participants

4

Conditions

Temperature
0 °C

Procedure

Ethyl 1-methyl-5-oxoprolinate (0.27 g, 1.58 mmol) was dissolved in ethanol (5 ml) and cooled to 0° C. in an ice bath. To this was added 2M aqueous sodium hydroxide solution (3 ml) and the mixture was stirred for ˜4 hours at 0° C. The ethanol was evaporated under vacuum and the aqueous residue was acidified with 2N aqueous hydrogen chloride to pH1. The volume of the aqueous phase was reduced to ˜3 ml under vacuum and then extracted with a 3:1 mixture of chloroform and isopropanol using a phase separator. The combined organic layers were concentrated to give 1-methyl-5-oxoproline which was used without further purification.

Workup

  1. customThe ethanol was evaporated under vacuum
  2. extractionextracted with a 3:1 mixture of chloroform and isopropanol using a phase separator
  3. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-28bbfc59df2c4c4395c4f787f1fda792
Source dataset
uspto-grants-2010_05
Patent number
US07718693B2

Linked notes

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