Ammonia → 1,4-Dioxaspiro[4.5]decan-8-amine

HRID 1942379Notes

Reaction equation

HRID 1942379 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[NH3:12].[H][H]>CO.[Pd]>[O:3]1[C:4]2([CH2:9][CH2:8][CH:7]([NH2:12])[CH2:6][CH2:5]2)[O:11][CH2:1][CH2:2]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 146343151,4-Dioxaspiro[4.5]decan-8-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 9.36 g (60 mmol) 1,4-cyclohexanedione monoethylene acetal in 60 mL of methanol which has been saturated with ammonia, 0.6 g of palladium on carbon (10%) is added. The mixture is stirred overnight under 4 bar hydrogen pressure. Filtration over Celite and concentration in vacuum provides the crude product in almost quantitative yield.

Workup

  1. additionis added
  2. filtrationFiltration
  3. concentrationover Celite and concentration in vacuum

Sources & evidence

ORD record
ord-87011bd0f9274964aadf68a2b588dff8
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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