Water → Tert-butyl 4-oxo-1-oxa-9-azaspiro(5.5)undecane-9-carboxylate

HRID 2040858Notes

Reaction equation

HRID 2040858 reaction equation
C=[C:2]1[CH2:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[O:5][CH2:4][CH2:3]1.I([O-])(=O)(=O)=[O:21].[Na+].O>O1CCOCC1.O.[Os](=O)(=O)(=O)=O.O>[O:21]=[C:2]1[CH2:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[O:5][CH2:4][CH2:3]1

Participants

7

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 57493826tert-Butyl 4-methylene-1-oxa-9-azaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 57493827Tert-butyl 4-oxo-1-oxa-9-azaspiro(5.5)undecane-9-carboxylateYield 59.5%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 30318Osmium TetroxideCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of Compound 29a (1.6 g, 5.99 mmol) in a mixture of dioxane-water (32.9 mL and 11 mL respectively) under stirring at r.t. was added a 4% sol. of osmium tetroxide in water (0.762 μL, 0.125 mmol). After 2 h, was added portionwise milled sodium metaperiodate (2.56 g, 12 mmol) affording a suspension that tended to become clear gray from brownish. After 4 h H2O was added, extracting with EtOAc, washing with H2O, drying over Na2SO4, evaporating the solvent to dryness. The residual tawny semi-solid was purified by means of automated flash chromatography (SP1®TM-Biotage; Petroleum Ether-EtOAc 7:3) to give 0.96 g of the title compound as a grey solid. Yield: 59.5%

Workup

  1. customaffording a suspension
  2. extractionextracting with EtOAc
  3. washwashing with H2O
  4. dry with materialdrying over Na2SO4
  5. customevaporating the solvent to dryness
  6. customThe residual tawny semi-solid was purified by means of automated flash chromatography (SP1®TM-Biotage; Petroleum Ether-EtOAc 7:3)

Sources & evidence

ORD record
ord-f280d6df0fe441bc9f7d4eb9c96d9a3c
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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