Isobutyl 3,4-epoxybutyrate → Oxiracetam

HRID 2291681Notes

Reaction equation

HRID 2291681 reaction equation
[NH:1]1C2(CCCCC2)[NH:4][CH2:3][C:2]1=[O:11].[O:12]1[CH2:22][CH:13]1[CH2:14][C:15]([O:17]CC(C)C)=O>C(O)(C)C.C(O)C>[CH2:14]1[C:15](=[O:17])[N:4]([CH2:3][C:2]([NH2:1])=[O:11])[CH2:22][CH:13]1[OH:12]

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 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

0.650 g 2,2-dimethyl-4-imidazolidinone ((5); R4 =R5 =CH3) (5.7 mmoles) is dissolved in 5 ml isopropanol. 1 g 2-methylpropyl 3,4-epoxybutanoate ((4); X=isobutyl) (6.32 mmoles) is added. The mixture is boiled for 9 h. A further 1 g of epoxyester is added and boiling is continued for a further 9 h. After cooling, the solvent is decanted and the dark mass obtained is taken up in ethanol. The solid obtained is filtered, to give oxiracetam, m.p. 167°-70° C.

Workup

  1. waitboiling is continued for a further 9 h
  2. temperatureAfter cooling
  3. customthe solvent is decanted
  4. customthe dark mass obtained
  5. customThe solid obtained
  6. filtrationis filtered

Sources & evidence

ORD record
ord-6d0cf8ab8074464783ed81a16b9788d3
Source dataset
uspto-grants-1989_01
Patent number
US04797496

Reaction notes

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