Process for the preparation of clausenamide
AssigneesBayer Aktiengesellschaft, Chinese Academy of Medical Sciences
InventorWolfgang Hartwig
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Abstract
A new synthetic route to clausenamide having the formula ##STR1## has been found. It has been found that a compound of the formula ##STR2## can be oxidized to provide the stereochemically correctly configured product, clasuenamide. A number of new compounds useful in the total synthesis of clausenamide have also been found. These compounds have the general formula ##STR3## wherein R is ##STR4## and CH.sub.2 OH.
Claims4
A process for the preparation of (.+-.)3(5*),4(R*), 5(R*), 7(5*)-3-hydroxy-5.alpha.-hydroxybenzyl-1-methyl-4-phenyl-pyrrolidin-2-one of the formula ##STR23## wherein (.+-.)4(R*), 5(R*), 7(5*)-5-.alpha.-hydroxybenzyl-1-methyl 4-phenylpyrrolidin-2-one of the formula ##STR24## is reacted with an oxidizing agent selected from the group consisting of peroxoacetic acid, chloroperbenzoic acid, molybdenum peroxide/pyridine complex, oxygen, ozone and sulphonyloxaziridine in an inert organic solvent in the presence of a base selected from the group consisting of an alkali metal alcoholate, an alkali metal amide, an alkali metal hydride, an organo-alkali metal compound, 1,5-diazabicyclo(4,3,0) non-5-ene and 1,8-diazabicyclo(5,4,0) undec-7-ene and further in the presence of a phosphite auxiliary, wherein the reaction is conducted at a temperature of -100.degree. C. to 20.degree. C., and wherein 1 to 5 moles of base are employed per mole of starting compound.
Dependencies are inferred from the claim text.