Reaction #710509

Reaction equation

adenosine

hydrogen peroxide

hydrogen peroxide

→

adenosine N1-oxide

Solvents

ethanol

acetic acid

Conditions

Workup

1. 1
   Filtrationfiltering the resultant
2. 2
   Otherto remove palladium carbon
3. 3
   Otherdrying the resulting solution in vacuo
4. 4
   workup.ADDITIONadding ethanol
5. 5
   Filtrationfiltering the resultant
6. 6
   Otherto obtain a crude crystalline adenosine N1-oxide
7. 7
   workup.DISSOLUTIONThe crude crystals were dissolved
8. 8
   Filtrationfiltered
9. 9
   Temperatureice chilled for crystallization
10. 10
    Otherthe recrystallization step twice

Procedure

Twenty grams of adenosine (commercialized by Sigma-Aldrich Corporation, St. Louis, Mo. USA, Product code: A9251-25G) was dispersed in one liter of acetic acid, admixed with 100 mL of hydrogen peroxide solution, and stirred at ambient temperature for five days. To the resulting solution was added five grams of 5% palladium on carbon, commercialized by Kawaken Fine Chemicals Co., Ltd, Tokyo, Japan, followed by decomposing an excessive amount of hydrogen peroxide, filtering the resultant to remove palladium carbon, drying the resulting solution in vacuo, adding ethanol to unstiffen the formed crystals, and filtering the resultant to obtain a crude crystalline adenosine N1-oxide. The crude crystals were dissolved by heating in two liters of ethanol, filtered, and ice chilled for crystallization, followed by repeating the recrystallization step twice to obtain eight grams of adenosine N1-oxide with a purity of 99.5%.

Source