Citric Acid → HCID 20741415, compound

HRID 348396Notes

Reaction equation

HRID 348396 reaction equation
[C:1]1([C:7]([C@H:9]2[CH2:13][N:12]([C@@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:11](=[O:22])[CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[OH:8][CH:7]([C@H:9]1[CH2:13][N:12]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:11](=[O:22])[CH2:10]1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 60123706HCID 60123706, compound

Product 1

HCID 20741415HCID 20741415, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an absolute ethanol (40 ml) solution of 4-(R)-phenylcarbonyl-1-[1-(R)-phenylethyl]-2-pyrrolidone (2.17 g, 7.40 mmol) was added sodium borohydride (280 mg) under ice cooling, followed by stirring at the same temperature for 1 hour. To the reaction solution was added 10% citric acid (50 ml) under ice cooling, and then the ethanol was removed under reduced pressure. The residue was extracted with chloroform (80 ml×2) and, after washing with saturated saline (100 ml), the organic layer was dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was subjected to silica gel column chromatography. Elution with eluents of n-hexane/ethyl acetate (1/3) to ethyl acetate (100%) afforded the low polar title compound having low polarity [F1] (892 mg, 41%) and the title compound having high polarity [F2] (1.163 g, 53%) as pale yellow oils.

Workup

  1. customthe ethanol was removed under reduced pressure
  2. extractionThe residue was extracted with chloroform (80 ml×2)
  3. washafter washing with saturated saline (100 ml)
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customAfter removal of the solvent under reduced pressure
  6. washElution with eluents of n-hexane/ethyl acetate (1/3) to ethyl acetate (100%)

Sources & evidence

ORD record
ord-8c547a751e424075b10ccaf4047bae29
Source dataset
uspto-grants-2007_02
Patent number
US07176313B2

Reaction notes

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