Isobutyl 3,4-epoxybutyrate → Oxiracetam

HRID 2291679Notes

Reaction equation

HRID 2291679 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>>[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

3

Reactant 2

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

Product 1

HCID 4626Oxiracetam

Procedure

1.3 g of 1,4-diazaspiro[4,5]decan-2-one ((5); R4 +R5 =--(CH2)5 --) (8.4 mmoles) are heated and stirred with magnetic stirring, with 1.5 g 2-methylpropyl 3,4-epoxybutanoate ((4), X=isobutyl) (9.5 mmoles) up to 110° (external temperature) for 24 h. The mixture is cooled, and the dark mass obtained is washed with 10 ml boiling ethyl acetate. This is decanted, and the solid obtained is crystallised from methanol to give oxiracetam as a crystalline white powder, m.p. 167°-70° C.

Workup

  1. temperatureThe mixture is cooled
  2. customthe dark mass obtained
  3. washis washed with 10 ml
  4. customThis is decanted
  5. customthe solid obtained
  6. customis crystallised from methanol

Sources & evidence

ORD record
ord-9101abfd1ed948a8b07f7b0e92ba1baf
Source dataset
uspto-grants-1989_01
Patent number
US04797496

Reaction notes

Loading…