Sodium periodate → Tert-butyl 4-(3-(ethoxycarbonyl)phenyl)-2-oxopiperidine-1-carboxylate

HRID 1816964Notes

Reaction equation

HRID 1816964 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].I([O-])(=O)(=O)=[O:26].[Na+]>C(Cl)(Cl)Cl.O.O.[Ru](=O)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C:14](=[O:26])[CH2:13]2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 57880576Tert-butyl 4-[3-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate

Product 1

HCID 57880492Tert-butyl 4-(3-(ethoxycarbonyl)phenyl)-2-oxopiperidine-1-carboxylateYield 29.5%

Reagents, catalysts & solvents 3

HCID 16211523Ruthenium dioxide hydrateCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of tert-butyl 4-[3-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate (48 g, 220 mmol) in chloroform (900 mL) was added ruthenium (IV) oxide hydrate (6.0 g, 45 mmol) followed by a solution of sodium periodate (150 g, 700 mmol) in water (900 mL). The resulting heterogenous reaction mixture was stirred at room temperature for 11 days before being filtered through a short column of celite. The organic layer was removed and the aqueous layer was extracted twice with DCM. The combined organic layers were washed with a 10% solution of sodium thiosulfate in water twice, and once with brine. This solution was dried over MgSO4, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography (silica gel, 20% EA/hexanes) to give 22.5 g (64.8 mmol) of tert-butyl 4-[3-(ethoxycarbonyl)phenyl]-2-oxopiperidine-1-carboxylate (29%).

Workup

  1. filtrationbefore being filtered through a short column of celite
  2. customThe organic layer was removed
  3. extractionthe aqueous layer was extracted twice with DCM
  4. washThe combined organic layers were washed with a 10% solution of sodium thiosulfate in water twice
  5. dry with materialThis solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by flash chromatography (silica gel, 20% EA/hexanes)

Sources & evidence

ORD record
ord-a83d38ae54a840c7bccd3fddbc52d1f5
Source dataset
uspto-grants-2009_10
Patent number
US07598243B2

Reaction notes

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