The reaction of 7-ethyl-10-hydroxycamptothecin (I) with phosgene gives 7-ethyl-10-(chlorocarbonyloxy)camptothecin (II), which is then condensed with 4-(1-piperidyl)piperidine.

The target compound has been obtained by condensation of 3.3-dimethylindoline-1-carbonyl chloride (IV) with endo-8-methyl-8-azabicyclo[3.2.1]octan-3-amine (II) by means of triethylamine followed by salification with HCl. The intermediates (II) and (IV) have been obtained as follows: A) The metthylation of 3-methylindole (III) with methylmagnesium iodid / methyl iodid, followed by hydrogenation with H2/Pt in acetic acid gives 3,3-dimethylindoline (I), which is then treated with phosghene / Et3N to afford intermediate (IV). B) The reductocondensation of 8-methyl-para-bicyclo[3.2.1]octan-3-one (V) with benzylamine and H2/Pt gives the secondary benzylamine (VI), which is finally deprotected by hydrogenation over Pd/C to give intermediate (II).

The target compound has been obtained by condensation of 3.3-dimethylindoline-1-carbonyl chloride (IV) with endo-8-methyl-8-azabicyclo[3.2.1]octan-3-amine (II) by means of triethylamine followed by salification with HCl. The intermediates (II) and (IV) have been obtained as follows: A) The metthylation of 3-methylindole (III) with methylmagnesium iodid / methyl iodid, followed by hydrogenation with H2/Pt in acetic acid gives 3,3-dimethylindoline (I), which is then treated with phosghene / Et3N to afford intermediate (IV). B) The reductocondensation of 8-methyl-para-bicyclo[3.2.1]octan-3-one (V) with benzylamine and H2/Pt gives the secondary benzylamine (VI), which is finally deprotected by hydrogenation over Pd/C to give intermediate (II).

The target compound has been obtained by condensation of 3.3-dimethylindoline-1-carbonyl chloride (IV) with endo-8-methyl-8-azabicyclo[3.2.1]octan-3-amine (II) by means of triethylamine followed by salification with HCl. The intermediates (II) and (IV) have been obtained as follows: A) The metthylation of 3-methylindole (III) with methylmagnesium iodid / methyl iodid, followed by hydrogenation with H2/Pt in acetic acid gives 3,3-dimethylindoline (I), which is then treated with phosghene / Et3N to afford intermediate (IV). B) The reductocondensation of 8-methyl-para-bicyclo[3.2.1]octan-3-one (V) with benzylamine and H2/Pt gives the secondary benzylamine (VI), which is finally deprotected by hydrogenation over Pd/C to give intermediate (II).

The target compound has been obtained by condensation of 3.3-dimethylindoline-1-carbonyl chloride (IV) with endo-8-methyl-8-azabicyclo[3.2.1]octan-3-amine (II) by means of triethylamine followed by salification with HCl. The intermediates (II) and (IV) have been obtained as follows: A) The metthylation of 3-methylindole (III) with methylmagnesium iodid / methyl iodid, followed by hydrogenation with H2/Pt in acetic acid gives 3,3-dimethylindoline (I), which is then treated with phosghene / Et3N to afford intermediate (IV). B) The reductocondensation of 8-methyl-para-bicyclo[3.2.1]octan-3-one (V) with benzylamine and H2/Pt gives the secondary benzylamine (VI), which is finally deprotected by hydrogenation over Pd/C to give intermediate (II).