Ethanol → ethyl (2R)-5-oxopyrrolidine-2-carboxylate

HRID 44810

Reaction equation

HRID 44810 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@@H:2]1[C:7]([OH:9])=[O:8].[CH3:10][CH2:11]O>S(=O)(=O)(O)O>[O:6]=[C:5]1[NH:1][C@@H:2]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 702EthanolHCID 439685D-Pyroglutamic acid

Product 1

HCID 643508ethyl (2R)-5-oxopyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of D-pyroglutamic acid (compound I-A, 20.4 g, 0.16 mol) in 100 mL of EtOH, 1.2 mL of conc. sulfuric acid was added. The mixture was heated under reflux overnight. Solvent was removed under reduced pressure to give (R)-ethyl 5-oxopyrrolidine-2-carboxylate (compound II-AA).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a7bce6362165468fa455f7ec24641f1b
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Linked notes

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