Sodium periodate → HCID 59456436, compound

HRID 2206945Notes

Reaction equation

HRID 2206945 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[C:7]1([CH3:36])[CH:12]=[CH:11][C:10]([S:13]([O:16][CH2:17][CH2:18][O:19][CH:20]2[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:22]([C:32]([O:34][CH3:35])=[O:33])[CH2:21]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1>O.ClCCl.O.[Ru](Cl)(Cl)Cl>[O:2]=[C:24]1[N:23]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH:22]([C:32]([O:34][CH3:35])=[O:33])[CH2:21][CH:20]1[O:19][CH2:18][CH2:17][O:16][S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH3:36])=[CH:8][CH:9]=1)(=[O:14])=[O:15]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 72330455HCID 72330455, compound

Product 1

HCID 59456436HCID 59456436, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.07 g (5.0 mmol) of sodium periodate and 0.338 g (0.15 mmol) of ruthenium(III) chloride hydrate in 12.5 ml of water was added to 0.44 g (1 mmol) of 1-tert-butyl 2-methyl 4-[2-(toluene-4-sulfonyloxy)ethoxy]pyrrolidine-1,2-dicarboxylate in 20 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 (20 ml) and the combined organic phases were stirred with 5 ml of isopropanol for 30 min. The mixture was dried over magnesium sulfate, filtered and the solvent was removed in vacuo. The crude product was purified by column chromatography (silica gel, hexane/ethyl acetate). 0.11 g (24%) of 1-tert-butyl 2-methyl 5-oxo-4-[2-(toluene-4-sulfonyloxy)ethoxy]pyrrolidine-1,2-dicarboxylate (23) was obtained as a colorless oil.

Workup

  1. customSubsequently, the phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate (20 ml)
  3. dry with materialThe mixture was dried over magnesium 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-a6a0b59009ed41c584ff8e3e79e29bae
Source dataset
uspto-grants-2016_06
Patent number
US09375497B2

Reaction notes

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