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

HRID 26185Notes

Reaction equation

HRID 26185 reaction equation
[CH3:1][CH2:2][CH:3]1[CH:15]([OH:16])[N:14]2[CH:6]3[CH:7]4[N:23]([CH3:24])[C:22]5[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=5[C:8]54[C@H:12]([OH:13])[CH:11]([CH:4]1[CH2:5]3)[CH:10]2[CH2:9]5.C(Cl)(Cl)Cl.ClC1C=CC=C(C(OO)=[O:37])C=1>CO>[CH3:1][CH2:2][C@H:3]1[CH:4]2[CH:11]3[C@@H:12]([OH:13])[C:8]45[C:17]6[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=6)[N:23]([CH3:24])[C@H:7]4[C@H:6]([CH2:5]2)[N+:14]([O-:37])([C@H:10]3[CH2:9]5)[C@@H:15]1[OH:16]

Participants

5

Reactant 3

HCID 6212Chloroform2×HCID 70297m-Chloroperbenzoic acidHCID 70691408(18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-14,18-diol

Product 1

HCID 3052184Ajmalan-17,21-diol, 4-oxide, (17R,21-alpha)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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%).

Workup

  1. temperaturethe mixture being cooled in ice

Sources & evidence

ORD record
ord-ab98f515c8fe4780b4e4bc4f224bc6f7
Source dataset
uspto-grants-1979_04
Patent number
US04148898

Reaction notes

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