Acetic Acid → Benzyl 9-oxo-3-azaspiro(5.5)undec-7-ene-3-carboxylate

HRID 574882Notes

Reaction equation

HRID 574882 reaction equation
N1([CH:7]=[C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:10][CH2:9]2)CCCCC1.[CH3:24][C:25](=[O:28])[CH:26]=[CH2:27].C(O)(=O)C>C(O)C>[O:28]=[C:25]1[CH2:24][CH2:7][C:8]2([CH2:9][CH2:10][N:11]([C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:12][CH2:13]2)[CH:27]=[CH:26]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6570Methyl vinyl ketoneHCID 86642880HCID 86642880, compound

Product 1

HCID 23435732Benzyl 9-oxo-3-azaspiro(5.5)undec-7-ene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of EXAMPLE 265A (15.88 g) in ethanol (300 mL) was added but-3-enone (3.89 g). The mixture was stirred at reflux overnight. Then acetic acid (30 mL) was added to the mixture which was stirred at reflux again overnight. The mixture was then concentrated under vacuum and the residue was diluted with ethyl acetate (400 mL) and washed with water and brine and dried over Na2SO4. After filtration and evaporation of the solvent, column purification gave the title compound.

Workup

  1. temperatureat reflux overnight
  2. stirringwas stirred
  3. temperatureat reflux again overnight
  4. concentrationThe mixture was then concentrated under vacuum
  5. additionthe residue was diluted with ethyl acetate (400 mL)
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration and evaporation of the solvent, column purification

Sources & evidence

ORD record
ord-82f77328746243d097e17b9475ab508b
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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