Methyl 1-benzyl-2,2-dimethyl-4,5-dioxopyrrolidine-3-carboxylate → 1-Benzyl-5,5-dimethylpyrrolidine-2,3-dione

HRID 1366614Notes

Reaction equation

HRID 1366614 reaction equation
[CH3:1][C:2]1([CH3:20])[CH:6](C(OC)=O)[C:5](=[O:11])[C:4](=[O:12])[N:3]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(O)=O.O>[CH3:1][C:2]1([CH3:20])[N:3]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:4](=[O:12])[C:5](=[O:11])[CH2:6]1

Participants

3

Reactant 1

HCID 66936588Methyl 1-benzyl-2,2-dimethyl-4,5-dioxopyrrolidine-3-carboxylate

Product 1

HCID 669359741-Benzyl-5,5-dimethylpyrrolidine-2,3-dioneYield 87.8%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of methyl 2,2-dimethyl-4,5-dioxo-1-(phenylmethyl)-3-pyrrolidinecarboxylate (5.6429 g, 20.50 mmol) in 10:1 HOAc-water (100 mL) was heated at 100° C. and stirred for 2 days. The solution was cooled to room temperature and concentrated in vacuo. The residue was partitioned between DCM (200 mL) and sat. aq. NaHCO3 (100 mL). The aqueous phase was extracted with a fresh portion of DCM (50 mL), and the combined organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give crude 5,5-dimethyl-1-(phenylmethyl)-2,3-pyrrolidinedione (3.9096 g, 88% crude yield) as a light orange solid. LCMS: (M+H)+: 218.1.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between DCM (200 mL) and sat. aq. NaHCO3 (100 mL)
  3. extractionThe aqueous phase was extracted with a fresh portion of DCM (50 mL)
  4. dry with materialthe combined organic phase was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10d4ee0f7379431f8f988ea19e69b0e3
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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