Methanol → HCID 13772856, compound

HRID 344229Notes

Reaction equation

HRID 344229 reaction equation
[C:1]1([C@@H:7]([N:9]2[C:13](=[O:14])[CH2:12][C@H:11]([C:15]([OH:17])=[O:16])[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:23]O>>[C:1]1([C@@H:7]([N:9]2[C:13](=[O:14])[CH2:12][C@H:11]([C:15]([O:17][CH3:23])=[O:16])[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 723630(3S)-5-Oxo-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxylic acid

Product 1

HCID 13772856HCID 13772856, compound

Procedure

(3S)-1-((S)-1-Phenylethyl)-5-oxo-3-pyrrolidinecarboxylic acid (666 g, optical purity not less than 99%) was dissolved in methanol (6 l), and conc. sulfuric acid (15 ml) was added at room temperature. The mixture was stirred at refluxing temperature for 7 hr. Methanol was evaporated, and the residue was extracted with ethyl acetate. The organic layer was washed with sodium hydrogencarbonate, dried over magnesium sulfate and concentrated under reduced pressure to give 738 g of methyl (3S)-1-((S)-1-phenylethyl)-5-oxo-3-pyrrolidine-carboxylate.

Workup

  1. temperatureat refluxing temperature for 7 hr
  2. customMethanol was evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with sodium hydrogencarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-737d2879531445e9bf38f47de4c0651f
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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