Ammonia → (3R,4S)-3,4-dimethylpyrrolidine-2,5-dione

HRID 2080661Notes

Reaction equation

HRID 2080661 reaction equation
N.[C:2]1([CH3:8])[CH:7]=CC=[CH:4][CH:3]=1.S(Cl)(Cl)=[O:10].C[N:14]([CH:16]=[O:17])C>>[CH3:4][C@H:3]1[C@@H:2]([CH3:8])[C:7](=[O:10])[NH:14][C:16]1=[O:17]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 1140TolueneHCID 6228DimethylformamideHCID 24386Thionyl Chloride

Product 1

HCID 642605(3R,4S)-3,4-dimethylpyrrolidine-2,5-dione

Conditions

Temperature
0 °C

Procedure

In a cooling bath, ammonia gas was introduced into a toluene (5 ml) solution of 390 mg of cis-2,3-dimethylsuccinic anhydride for 30 minutes. The solvent was evaporated away under reduced pressure to obtain a white solid. This was dissolved in 10 ml of DMF, and at −78° C., 0.5 ml of thionyl chloride was added to it and stirred at 0° C. for 2 hours. The reaction liquid was restored to room temperature, the solvent was evaporated away under reduced pressure, ethyl acetate was added to the residue, and washed with aqueous saturated sodium hydrogencarbonate solution. After dried, the solvent was removed, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=7/3 to 0/1) to obtain 269 mg of the entitled compound as a white solid.

Workup

  1. customThe solvent was evaporated away under reduced pressure
  2. customto obtain a white solid
  3. customThe reaction liquid
  4. customwas restored to room temperature
  5. customthe solvent was evaporated away under reduced pressure, ethyl acetate
  6. additionwas added to the residue
  7. washwashed with aqueous saturated sodium hydrogencarbonate solution
  8. customAfter dried
  9. customthe solvent was removed
  10. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=7/3 to 0/1)

Sources & evidence

ORD record
ord-aa2fd2f5cce44f69821c5f5adbfdb9e6
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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