Water → 1-(tert-Butyl) 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate

HRID 889055Notes

Reaction equation

HRID 889055 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:22][O:23][C:24]([CH:26]1[CH2:30][C:29](=O)[CH2:28][N:27]1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:25].CC(C)([O-])C.[K+].O>C1COCC1>[CH3:22][O:23][C:24]([CH:26]1[CH2:30][C:29](=[CH2:2])[CH2:28][N:27]1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 638159Methyltriphenylphosphonium iodideHCID 42518531-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 592637351-(tert-Butyl) 2-methyl 4-methylenepyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyltriphenylphosphonium iodide (1.25 g, 3.08 mmol) in THF (20 ml) at 0° C., 4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (500 mg, 2.05 mmol) and potassium ter-butoxide (460 mg, 4.11 mmol) was added. It was stirred for overnight at room temperature. Water was added and the compound was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulphate, filtered and concentrated under vacuum. Purification by column chromatography offered 4-methylene-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester as a colorless oil (0.23 g, 46%).

Workup

  1. extractionthe compound was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-4a4480769e4243c08820cccc79b5fdc1
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

Loading…