Isobutyl 3,4-epoxybutyrate → Oxiracetam

HRID 2291686Notes

Reaction equation

HRID 2291686 reaction equation
[NH:1]1C2(CCCCC2)[NH:4][CH2:3][C:2]1=[O:11].CC(C)CO[C:16](=[O:21])[CH2:17][CH:18]1[O:20][CH2:19]1>O.CC(C)=O>[CH2:17]1[C:16](=[O:21])[N:4]([CH2:3][C:2]([NH2:1])=[O:11])[CH2:19][CH:18]1[OH:20]

Participants

5

Reactant 2

HCID 5463767Isobutyl 3,4-epoxybutyrateHCID 131250391,4-Diazaspiro[4.5]decan-2-one

Product 1

HCID 4626Oxiracetam

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

19 g 2-(1-Methylethyl)imidazolidinone ((5); R4 =H, R5 =isopropyl) (0.15 moles) are dissolved in 100 ml water and 150 ml acetone. 2-Methylpropyl-3,4-epoxybutanoate (0.15 moles) are added and the mixture is heated and stirred for 48 h at 70° C. The acetone is evaporated in vacuo and 100 ml DMF are added, followed by boiling for 21 h. The mixture is reduced to a small volume in vacuo, the residue is taken up with 40 ml water and washed with 2×40 ml methylene chloride. The aqueous phase is evaporated to dryness and redissolved in 15 ml methanol. This is left to stand for 3 h at 0° C., filtered and dried to give oxiracetam as a white crystalline powder, m.p. 167°-70° C.

Workup

  1. temperaturethe mixture is heated
  2. customThe acetone is evaporated in vacuo and 100 ml DMF
  3. additionare added
  4. waitby boiling for 21 h
  5. washwashed with 2×40 ml methylene chloride
  6. customThe aqueous phase is evaporated to dryness
  7. dissolutionredissolved in 15 ml methanol
  8. waitThis is left
  9. waitto stand for 3 h at 0° C.
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-49690035c3a04da091db851f55d062f6
Source dataset
uspto-grants-1989_01
Patent number
US04797496

Reaction notes

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