Citric Acid → HCID 20741415, compound

HRID 1883960Notes

Reaction equation

HRID 1883960 reaction equation
[BH4-].[Na+].[C:3]1([C:9]([C@H:11]2[CH2:15][N:14]([C@@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])[C:13](=[O:24])[CH2:12]2)=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[OH:10][CH:9]([C@H:11]1[CH2:15][N:14]([C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])[C:13](=[O:24])[CH2:12]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=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

Under ice-cooling, sodium borohydride (280 mg) was added to anhydrous ethanol (40 ml) solution of 4-(R)-phenylcarbonyl-1-[1-(R)-phenylethyl]-2-pyrrolidone (2.17 g, 7.40 mmol), and the mixture was stirred at the same temperature for 1 hour. The reaction solution was mixed with 10% citric acid (50 ml) under ice-cooling and then ethanol was evaporated under a reduced pressure. The residue was extracted with chloroform (80 ml×2), and the organic layer was washed with saturated brine (100 ml) and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the resulting residue was applied to a silica gel column chromatography. By eluting with n-hexane:ethyl acetate (1:3) to ethyl acetate (100%), 892 mg (41%) of the low polarity title compound [F1] and then 1.163 g (53%) of the high polarity title compound [F2] were respectively obtained each as a light yellow oil.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturecooling
  3. customethanol was evaporated under a reduced pressure
  4. extractionThe residue was extracted with chloroform (80 ml×2)
  5. washthe organic layer was washed with saturated brine (100 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under a reduced pressure
  8. washBy eluting with n-hexane:ethyl acetate (1:3) to ethyl acetate (100%), 892 mg (41%) of the low polarity title compound [F1]

Sources & evidence

ORD record
ord-df96b808f6d04cbab87b720141315cc4
Source dataset
uspto-grants-2004_07
Patent number
US06762181B1

Reaction notes

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