Water → Ammonia

HRID 36008Notes

Reaction equation

HRID 36008 reaction equation
[C:1]([N:4]1[CH2:15][CH2:14][C:7]2([O:11][CH2:10][CH:9]([OH:12])[CH:8]2[CH3:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH3:4].[C:1]([N:4]1[CH2:5][CH2:6][C:7]2([O:11][CH2:10][CH:9]([OH:12])[CH:8]2[CH3:13])[CH2:14][CH2:15]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 14852048HCID 14852048, compoundHCID 21226445Aluminium lithium hydride

Product 2

HCID 222AmmoniaHCID 14852048HCID 14852048, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.83 g 8-acetyl-3-hydroxy-4-methyl-1-oxa-8-azaspiro[4,5]decane (B) in 20 ml anhydrous tetrahydrofuran was added dropwise to a mixture of 1.01 g lithium aluminum hydride and 25 ml tetrahydrofuran, and the resulting mixture was heated under reflux for three hours and then cooled in ice. Water (1.1 ml) and 10% caustic soda solution (1.1 ml) were slowly added in that order, the reaction mixture was filtered through Celite, and the insoluble matters were thoroughly washed with tetrahydrofuran and ethyl acetate. The washings were joined to the filtrate, the combined solution was concentrated, and the residue was subjected to silica gel column chromatography using, as eluent, a mixed solvent of chloroform/methanol/conc. ammonia (40:10:1), giving 8-ethyl-3-hydroxy-4-methyl-1-oxa-8-azaspiro[4,5]decane (B) as oil. It was converted to its hydrochloride by treatment with methanolic hydrogen chloride. Yield: 0.4 g, m.p.: 150°-155° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for three hours
  3. temperaturecooled in ice
  4. filtrationthe reaction mixture was filtered through Celite
  5. washthe insoluble matters were thoroughly washed with tetrahydrofuran and ethyl acetate
  6. concentrationthe combined solution was concentrated

Sources & evidence

ORD record
ord-26dfa0e640964d4eb54385b7a5a842c2
Source dataset
uspto-grants-1995_05
Patent number
US05412096

Reaction notes

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