Ethyl Acetate → (4R)-1-((R)-1-(4-methoxyphenyl)ethyl)-4-(oxiran-2-yl)pyrrolidin-2-one

HRID 2208977Notes

Reaction equation

HRID 2208977 reaction equation
[I-].C[S+](C)(C)=O.[H-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]([N:19]2[C:23](=[O:24])[CH2:22][C@@H:21]([CH:25]=[O:26])[CH2:20]2)[CH3:18])=[CH:13][CH:12]=1.[CH3:27]COC(C)=O>CS(C)=O>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]([N:19]2[CH2:20][C@H:21]([CH:25]3[CH2:27][O:26]3)[CH2:22][C:23]2=[O:24])[CH3:18])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 117842859(R)-1-((R)-1-(4-Methoxyphenyl)ethyl)-5-oxopyrrolidine-3-carbaldehyde

Product 1

HCID 117843249(4R)-1-((R)-1-(4-methoxyphenyl)ethyl)-4-(oxiran-2-yl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To suspension of trimethylsulfoxonium iodide (579 mg, 2.63 mmol) in DMSO (5 mL) was added NaH (60%, 116 mg, 2.89 mmol), and the reaction was stirred for 30 minutes. A solution of (R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidine-3-carbaldehyde 1.07 (650 mg, 2.63 mmol) in DMSO (5 mL) was added and the reaction was stirred for 30 minutes at 0° C. The reaction was poured into ice water (20 mL) and EtOAc (20 mL) was added. The aqueous layer was extracted with EtOAc (3×25 mL), and the combined organics were dried (MgSO4), filtered and concentrated. Flash chromatography (50→100% EtOAc in hexanes) provided (4R)-1-((R)-1-(4-methoxyphenyl)ethyl)-4-(oxiran-2-yl)pyrrolidin-2-one 1.13.

Workup

  1. stirringthe reaction was stirred for 30 minutes at 0° C
  2. additionwas added
  3. extractionThe aqueous layer was extracted with EtOAc (3×25 mL)
  4. dry with materialthe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-059056d1607d405db7d4a666cf8c3308
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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