Water → HCID 55287169, compound

HRID 1055904Notes

Reaction equation

HRID 1055904 reaction equation
[O:1]=[C:2]1[CH:9](C(OCC)=O)[C:8](=[O:15])[C:5]2([CH2:7][CH2:6]2)[CH2:4][NH:3]1.O>C(#N)C>[CH2:6]1[C:5]2([C:8](=[O:15])[CH2:9][C:2](=[O:1])[NH:3][CH2:4]2)[CH2:7]1

Participants

4

Reactant 2

HCID 962WaterHCID 89782026HCID 89782026, compound

Product 1

HCID 55287169HCID 55287169, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 6,8-dioxo-5-azaspiro[2.5]octane-7-carboxylate (4.0 g, 18.95 mmol) was taken up in ACN containing 1% v/v water (40 mL) and the resulting solution was heated at 90° C. for 3 h. The mixture was cooled to RT and concentrated in vacuo. The residue was diluted with water (40 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 80% EtOAc/petroleum ether) furnished 5-azaspiro[2.5]octane-6,8-dione (1.2 g, 8.62 mmol, 46% yield) as a pale pink solid: 1H NMR (400 MHz, CDCl3): δ 8.24 (br s, 1H), 3.41 (s, 2H), 3.33-3.31 (m, 2H), 1.11-1.05 (m, 2H), 0.98-0.96 (m, 2H). m/z (ESI, +ve) 140.3 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to RT
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water (40 mL)
  4. extractionextracted with EtOAc (2×50 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customChromatographic purification of the residue (silica gel, 80% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-97ebf55d73bf403280cdbb9ca3b1f5e1
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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