Chloroform → Ajmalan-17,21-diol, 4-oxide, (17R,21-alpha)-

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Reaction Steps

200 mg of ajmaline were put in solution in an organic solvent such as chloroform or a mixture of chloroform and methanol (5 ml). A solution of 200 mg of metachloroperbenzoic acid in 5 ml of the same solvent was slowly added, with stirring, the mixture being cooled in ice. The kinetics of the reaction were followed by thin layer chromatography (alkaline Kieselgel plate; solvent CHCl3 90-MeOH 10). At the same time as the N-oxy-ajmaline, there were formed more polar secondary products, already in a important amount whereas the whole of the ajmaline was not yet transformed. The solution was diluted with chloroform, washed with an 15% aqueous solution of KHCO3, dried, filtered and dry distilled. The residue obtained, chromatographed on a silica column of activity V, gave 104 mg of N-oxyajmaline (Yield 49.5%).

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