Sodium ethoxide → HCID 89782026, compound

HRID 1055903Notes

Reaction equation

HRID 1055903 reaction equation
[O-]CC.[Na+].[CH2:5]([O:7][C:8](=[O:22])[CH2:9][C:10]([NH:12][CH2:13][C:14]1([C:17]([O:19]CC)=O)[CH2:16][CH2:15]1)=[O:11])[CH3:6]>C1(C)C=CC=CC=1.O>[O:11]=[C:10]1[CH:9]([C:8]([O:7][CH2:5][CH3:6])=[O:22])[C:17](=[O:19])[C:14]2([CH2:15][CH2:16]2)[CH2:13][NH:12]1

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 69183026HCID 69183026, compound

Product 1

HCID 89782026HCID 89782026, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a freshly prepared solution of sodium ethoxide [made from sodium (21 mg, 0.9338 mmol) and EtOH (0.5 mL)] was added a solution of ethyl 1-((3-ethoxy-3-oxopropanamido)methyl)cyclopropanecarboxylate (200 mg, 0.7782 mmol) in toluene (2 mL), and the resulting mixture was heated at reflux for 4 h. The mixture was cooled to RT, diluted with water (5 mL), and extracted with EtOAc (2×5 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to provide ethyl 6,8-dioxo-5-azaspiro[2.5]octane-7-carboxylate (150 mg, 0.710 mmol, 91% yield): m/z (ESI, +ve) 212.3 (M+H)+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 4 h
  3. extractionextracted with EtOAc (2×5 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c8c44d8cc7346e7b74a9f5383d8fa61
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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