Sodium periodate → HCID 57486897, compound

HRID 15357Notes

Reaction equation

HRID 15357 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH3:14])[C:10]2=[O:13])=[CH:5][CH:4]=1)=C.I([O-])(=O)(=O)=[O:16].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:14][N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([CH:1]=[O:16])=[CH:4][CH:5]=2)[C:10]1=[O:13]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 57486896HCID 57486896, compound

Product 1

HCID 57486897HCID 57486897, compoundYield 74.3%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 7-ethenyl-2-methyl-3,4-dihydro-1(2H)-isoquinolinone (181 mg, 0.968 mmol) in 1,4-dioxane (I 5 ml) and water (3 ml) at 0° C. was added sodium periodate (476 mg, 2.226 mmol) and osmium tetroxide (1.1 ml of a 4% aqueous solution). The reaction mixture was warmed to room temperature and stirred for 0.5 h before evaporation of the reaction mixture. The residue was dissolved in 1,4-dioxane (20 ml) and evaporated again. The mixture was then dissolved in dichloromethane (100 ml), dried with magnesium sulphate and evaporated. Chromatography on silica, eluting with 0-100% Ethyl Acetate/Hexane, gave the product (136 mg, 74%).

Workup

  1. customevaporated again
  2. dissolutionThe mixture was then dissolved in dichloromethane (100 ml)
  3. dry with materialdried with magnesium sulphate
  4. customevaporated
  5. washChromatography on silica, eluting with 0-100% Ethyl Acetate/Hexane

Sources & evidence

ORD record
ord-1a0630ac4be84d248f19bb2f3f739427
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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