Preparation of two metabolites of isometheptene

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Abstract
Trans-(E)-2-Methyl-6-methylamino-2-hepten-1-ol (6) and cis-(Z)-2-methyl-6-methylamino-2-hepten-1-ol (13), two in vivo metabolites from the antispasmodic agent isometheptene (2), ((±)–N,1,5-trimethyl-4-hexenylamine) have been synthesized. In the first synthesis of the trans isomer, the N-trifluoroacetyl derivative of 2 was oxidized with selenium dioxide in ethanol to give trans-2-methyl-6-N-methyltrifluoroacetamido-2-hepten-1-al (4). Aldehyde (4) was converted to 6 by reaction with sodium borohydride in ethanol. In the second synthesis, trans-2-methyl-6-oxo-2-hepten-1-ol ethylene ketal (8) and cis-2-methyl-6-oxo-2-hepten-1-ol ethylene ketal (11) were hydrolyzed without isomerization to hydroxyketones 9 and 12. Both 9 and 12 were reductively aminated to the desired metabolites, 6 and 13.

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