Sodium Hydroxide → (2S)-1-methyl-5-oxopyrrolidine-2-carboxylic acid
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe ethanol was evaporated under vacuum
- extractionextracted with a 3:1 mixture of chloroform and isopropanol using a phase separator
- concentrationThe combined organic layers were concentrated
Sources & evidence
- ORD record
- ord-acfa93724bc2414eb4f16580866091d3
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08048907B2
Reaction notes
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