1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate → HCID 67386995, compound

HRID 590664Notes

Reaction equation

HRID 590664 reaction equation
[CH3:1][C:2]([O-])(C)C.[K+].O=[C:8]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:10]([C:20]([O:22][CH3:23])=[O:21])[CH2:9]1>C1COCC1>[CH:1](=[C:8]1[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:10]([C:20]([O:22][CH3:23])=[O:21])[CH2:9]1)[CH3:2]

Participants

4

Reactant 2

HCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67386995HCID 67386995, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Ph3PEtBr (84 g, 227 mmol) and KOtBu (76.7 g, 556 mmol) in THF (1100 mL) was stirred at rt under nitrogen atmosphere for 1 h, and then added (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (50 g, 206 mmol) in THF (350 mL) dropwise. The mixture was stirred at room temperature for 4 hs. TLC showed the reaction was completed. The mixture was quenched with NH4Cl aqueous and concentrated to remove THF, and then dissolved in EtOAc and water. The combined organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (PE: EtOAc=30:1 to 5:1) to afford (S)-1-tert-butyl 2-methyl 4-ethylidenepyrrolidine-1,2-dicarboxylate (18.3 g, 35%) as yellow oil.

Workup

  1. customThe mixture was quenched with NH4Cl aqueous
  2. concentrationconcentrated
  3. customto remove THF
  4. dissolutiondissolved in EtOAc
  5. washThe combined organic layer was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (PE: EtOAc=30:1 to 5:1)

Sources & evidence

ORD record
ord-a0fb9a502da84d248f59fbbf716fca17
Source dataset
uspto-grants-2016_01
Patent number
US09233974B2

Reaction notes

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