Sodium periodate → Tert-butyl 2-(4-formyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1848500Notes

Reaction equation

HRID 1848500 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][N:3]1[C:19]1[CH2:20][O:21][C:22](=[O:26])[C:23]=1[CH:24]=C.I([O-])(=O)(=O)=[O:28].[Na+]>CC(C)=O.O>[CH:24]([C:23]1[C:22](=[O:26])[O:21][CH2:20][C:19]=1[N:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)[C:2]1=[O:1])=[O:28]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 86709509Tert-butyl 1-oxo-2-(5-oxo-4-vinyl-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 86709510Tert-butyl 2-(4-formyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

tert-butyl 1-oxo-2-(5-oxo-4-vinyl-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate (1.6 g, 4.4 mmol) was dissolved in acetone (36 mL) and water (36 mL), then K2OsO4.2H2O was added and the mixture was stirred for ˜5 min. Solid sodium periodate (3.77 g, 17.6 mmol) was added in 4 portions during 1 hour and the reaction temperature was maintained below 40° C. using an ice-bath. The resulting mixture was stirred for 1 hour at room temperature. LCMS after 2 hours showed complete consumption of starting material. The suspension was filtered and the filtrate was concentrated to remove acetone. The aqueous layer was extracted with DCM (3×). Combined organic layers were washed with 10% Na2S2O3 solution (2×), dried over anhydrous Na2SO4, filtered, concentrated to obtain the title compound, which was taken to the next step without further purification.

Workup

  1. temperaturethe reaction temperature was maintained below 40° C.
  2. stirringThe resulting mixture was stirred for 1 hour at room temperature
  3. waitLCMS after 2 hours showed complete
  4. customconsumption of starting material
  5. filtrationThe suspension was filtered
  6. concentrationthe filtrate was concentrated
  7. customto remove acetone
  8. extractionThe aqueous layer was extracted with DCM (3×)
  9. washCombined organic layers were washed with 10% Na2S2O3 solution (2×)
  10. dry with materialdried over anhydrous Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-f34a11b7f3164c70baee3730c4cae77d
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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