Potassium Hydroxide → 1,4-Dioxa-8-azaspiro[4.6]undecane

HRID 968486Notes

Reaction equation

HRID 968486 reaction equation
[O:1]1[C:5]2([CH2:11][CH2:10][CH2:9][N:8](C(OCC)=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[OH-].[K+]>CC(O)C>[O:1]1[C:5]2([CH2:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69282947Ethyl 1,4-dioxa-8-azaspiro[4.6]undecane-8-carboxylate

Product 1

HCID 216795911,4-Dioxa-8-azaspiro[4.6]undecaneYield 62.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of intermediate (4) (0.585 mol) and KOH (5.85 mol) in 2-propanol (1200 ml) was stirred and refluxed overnight. The solvent was evaporated. The residue was stirred in water and this mixture was extracted with DCM. The separated organic layer was dried, filtered, and the solvent evaporated, yielding 57.7 g of 1,4-dioxa-8-azaspiro[4.6]undecane (intermediate 5).

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. stirringThe residue was stirred in water
  4. extractionthis mixture was extracted with DCM
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-0879ae058660484dbe63ef8f53bffb91
Source dataset
uspto-grants-2007_12
Patent number
US07304052B2

Reaction notes

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