Sodium periodate → HCID 86588174, compound

HRID 1760369Notes

Reaction equation

HRID 1760369 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:10][CH2:9][CH2:8][N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]=C)=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:5])[CH3:2].I([O-])(=O)(=O)=[O:32].[Na+]>[Os](=O)(=O)(=O)=O.O1CCOCC1.O>[CH2:29]([O:28][C:26]([C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][CH2:9][CH2:8][N:7]1[C:11]1[CH:12]=[N:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[O:32])=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:27])[CH3:30]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 69743649HCID 69743649, compound

Product 1

HCID 86588174HCID 86588174, compoundYield 98.7%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 1-[6-(4-Vinyl-phenoxy)-pyridin-3-yl]-pyrrolidine-2,2-dicarboxylic acid diethyl ester (4.8 g, 11.3 mmol), sodium metaperiodate (4.8 g, 22 mmol), osmium tetroxide (10 mg) and 2:1 dioxane-water (189 mL) was stirred for 6 hours at ambient temperature. The mixture was quenched with sodium sulfite, diluted with water and extracted 3× with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated in vacuo affording 1-[6-(4-Formyl-phenoxy)-pyridin-3-yl]-pyrrolidine-2,2-dicarboxylic acid diethyl ester as a colorless syrup (4.6 g).

Workup

  1. customThe mixture was quenched with sodium sulfite
  2. additiondiluted with water
  3. extractionextracted 3× with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0ebaae6dcff4227a53ebc12dd8ef6fd
Source dataset
uspto-grants-2005_01
Patent number
US06841671B2

Reaction notes

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