Sodium periodate → 1-(Benzenesulfonyl)-5-hydroxypyrrolidin-2-one

HRID 1761888Notes

Reaction equation

HRID 1761888 reaction equation
[C:1]1([S:7]([N-:10][C:11](=[O:16])[CH2:12][CH2:13][CH:14]=C)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([O-])(=O)(=O)=[O:18].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[C:1]1([S:7]([N:10]2[CH:11]([OH:16])[CH2:12][CH2:13][C:14]2=[O:18])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodate2×HCID 178447417HCID 178447417, compound

Product 1

HCID 30867291-(Benzenesulfonyl)-5-hydroxypyrrolidin-2-oneYield 40.5%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

50 mg of osmium tetraoxide is added to a solution of 5 g of N-benzenesulphonyl-4-pentenoylamide in 150 cm3 of dioxan and 50 cm3 of water. After about 20 minutes, 5.10 g of sodium metaperiodate is added, and after agitating for 1 hour, a further 5.10 g of sodium metaperiodate is added, with agitation for a further 2 hours at ambient temperature. The precipitate formed is filtered off, the filtrate is evaporated to dryness and the residue is dissolved in 50 cm3 of ethyl acetate, treated with activated charcoal, then evaporated to dryness. The residue is triturated in anhydrous ethyl ether, and 2.05 g of the expected product is obtained, which is re-crystallizxed from isopropanol m.p. 121° C.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. customthe filtrate is evaporated to dryness
  4. dissolutionthe residue is dissolved in 50 cm3 of ethyl acetate
  5. additiontreated with activated charcoal
  6. customevaporated to dryness
  7. customThe residue is triturated in anhydrous ethyl ether

Sources & evidence

ORD record
ord-218380039bd4432e9995d5892da13026
Source dataset
uspto-grants-1989_05
Patent number
US04829079

Reaction notes

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