Acetic Acid → 2,2-Diethyl 1-acetyl-5-hydroxy-3-phenyl-2,2-pyrrolidinedicarboxylate

HRID 1099201Notes

Reaction equation

HRID 1099201 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[Na].[CH:17](=[O:26])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)(=O)C>C(O)C>[C:1]([N:4]1[CH:17]([OH:26])[CH2:18][CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3073-Phenylprop-2-EnalHCID 14041Acetamidomalonic acid diethyl esterHCID 5360545Sodium

Product 1

HCID 6589632,2-Diethyl 1-acetyl-5-hydroxy-3-phenyl-2,2-pyrrolidinedicarboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of diethyl acetamidomalonate (75.0 g, 345 mmol) in ethanol (375 ml) at 0° C. was added sodium metal (6.9 g, 36 mmol). Cinnamaldehyde (50.0 g, 378 mmol) was added dropwise to the resulting solution. The reaction was warmed to rt and allowed to stir for 2 h. Acetic acid (7 ml) was added, and the solution was concentrated. The residue was dissolved in EtOAc, washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude solid was triturated with hexanes/EtOAc to yield diethyl 1-acetyl-5-hydroxy-3-phenylpyrrolidine-2,2-dicarboxylate as a white solid (96%).

Workup

  1. concentrationthe solution was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude solid was triturated with hexanes/EtOAc

Sources & evidence

ORD record
ord-ef507f4134c54b9393b96459eb7471b9
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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