Citric Acid → HCID 57758657, compound

HRID 229550Notes

Reaction equation

HRID 229550 reaction equation
[O:1]=[C:2]1[N:6]([C@@H:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:8])[CH2:5][CH:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.C=O.[H-].[Na+].C(O)(=O)C[C:28](CC(O)=O)(C(O)=O)[OH:29]>CN(C)C=O>[OH:29][CH2:28][C@:4]1([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:3][C:2](=[O:1])[N:6]([C@@H:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:8])[CH2:5]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 712FormaldehydeHCID 24758Sodium hydrideHCID 57758674HCID 57758674, compound

Product 1

HCID 57758657HCID 57758657, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate (4.00 g, 13.8 mmol) in N,N-dimethylformamide (40 mL), paraformaldehyde (0.830 g, 27.7 mmol) and sodium hydride (0.600 g, 55% in oil, 13.8 mmol) were added at room temperature, and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture, 10% aqueous solution of citric acid (150 mL) was added in an ice bath, and the solution was extracted with ethyl acetate (300 mL×2). The organic layer was washed with water (100 mL×2) and saturated aqueous solution of sodium chloride (100 mL), and dried with anhydrous sodium sulfate. After the filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elusion by hexane:ethyl acetate, 7:3→1:4) to obtain 1.03 g (23%) of the title compound as a white solid.

Workup

  1. extractionthe solution was extracted with ethyl acetate (300 mL×2)
  2. washThe organic layer was washed with water (100 mL×2) and saturated aqueous solution of sodium chloride (100 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationAfter the filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (elusion by hexane:ethyl acetate, 7:3→1:4)

Sources & evidence

ORD record
ord-0f05e192b23348e9bc58e2c0054ea303
Source dataset
uspto-grants-2009_07
Patent number
US07563805B2

Reaction notes

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