Sodium periodate → HCID 58240599, compound

HRID 2206947Notes

Reaction equation

HRID 2206947 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[F:7][CH2:8][CH2:9][O:10][CH:11]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:13]([C:23]([O:25][CH3:26])=[O:24])[CH2:12]1>O.ClCCl.O.[Ru](Cl)(Cl)Cl>[F:7][CH2:8][CH2:9][O:10][CH:11]1[C:15](=[O:2])[N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:13]([C:23]([O:25][CH3:26])=[O:24])[CH2:12]1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 72330453HCID 72330453, compound

Product 1

HCID 58240599HCID 58240599, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4.3 g (20.0 mmol) of sodium periodate and 1.7 g (0.6 mmol) of ruthenium(III) chloride hydrate in 50 ml of water was added to 1.45 g (5 mmol) of 1-tert-butyl 2-methyl 4-(2-fluoroethoxy)pyrrolidine-1,2-dicarboxylate in 80 ml of dichloromethane. The mixture was left at room temperature for three days with vigorous stirring. Subsequently, the phases were separated, the aqueous phase was extracted twice with ethyl acetate (25 ml) and the combined organic phases were stirred with 10 ml of isopropanol for 30 min. The mixture was dried over sodium sulfate, filtered and the solvent was removed in vacuo. The crude product was purified by column chromatography (silica gel, hexane/ethyl acetate). 0.26 g (17%) of 1-tert-butyl 2-methyl 4-(2-fluoroethoxy)-5-oxopyrrolidine-1,2-dicarboxylate (26) was obtained as.

Workup

  1. customSubsequently, the phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate (25 ml)
  3. dry with materialThe mixture was dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe crude product was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-457414afe7e24f35acf190c5a7670f2d
Source dataset
uspto-grants-2016_06
Patent number
US09375497B2

Reaction notes

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