Hydrogen Peroxide → Tert-butyl 3-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylate

HRID 2300178

Reaction equation

HRID 2300178 reaction equation
[O:1]=[C:2]1[CH2:5][C:4]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:3]1.OO.[OH-].[Na+].O.O.O.O.O.S([O-])([O-])(=[O:29])=S.[Na+].[Na+]>CO.O.C(OCC)(=O)C>[O:29]=[C:2]1[CH2:3][C:4]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:5][O:1]1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 61475Sodium Thiosulfate PentahydrateHCID 11195798Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 22744536Tert-butyl 3-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

567 ml solution of 37.8 g tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate in methanol was cooled on ice water, and 43 g of 30% aqueous hydrogen peroxide was added dropwise thereinto. 63 ml of 1 N aqueous sodium hydroxide was added dropwise thereto, and the mixture was stirred at room temperature for 2 hr. 1000 ml ethyl acetate, 600 ml water and 100 ml saturated aqueous sodium thiosulfate pentahydrate were added thereto, and the organic layer was recovered. The extracted solution was washed with brine, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was evaporated to give 28.4 g of tert-butyl 3-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylate.

Workup

  1. additionwas added dropwise
  2. customthe organic layer was recovered
  3. washThe extracted solution was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9c29fa327797484b8840f6e8c2c0be30
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Linked notes

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