Water → Octane

HRID 1975331Notes

Reaction equation

HRID 1975331 reaction equation
[CH2:1]1[C:3]2([C:8](=O)[NH:7][CH2:6][C:5](=O)[NH:4]2)[CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:2][CH2:1][CH2:3][CH2:8][CH2:2][CH2:1][CH2:3][CH3:8].[CH2:2]1[C:3]2([CH2:8][NH:7][CH2:6][CH2:5][NH:4]2)[CH2:1]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 153380054,7-Diazaspiro[2.5]octane-5,8-dioneHCID 21226445Aluminium lithium hydride

Product 2

HCID 356OctaneHCID 153380064,7-Diazaspiro[2.5]octane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

350 mg of compound 24 was suspended in 200 ml of dry tetrahydrofuran followed by the addition of 0.6 g of lithium aluminum hydride. The mixture was refluxed for 14 hours. To this reaction mixture was then added 0.6 g of water, 0.6 g of 15% aqueous sodium hydroxide and 1.8 g of water in the order mentioned under ice-cooling and the resulting precipitate was removed by filtration. The precipitate was thoroughly washed with tetrahydrofuran and ether and the washings and the filtrate were combined. The solvent was then removed under reduced pressure to give title compound 4,7-diazaspiro[2,5]octane 25 as a crude product. This product was subjected, without purification, to the substitution reaction.

Workup

  1. temperatureThe mixture was refluxed for 14 hours
  2. temperaturecooling
  3. customthe resulting precipitate was removed by filtration
  4. washThe precipitate was thoroughly washed with tetrahydrofuran and ether
  5. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-6ebc3299f6e24a1084c227ae4461c55b
Source dataset
uspto-grants-1994_02
Patent number
US05286723

Reaction notes

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