Organic Process Research & Development · 2003 · 35 citations · 11 references
Combinatorial ChemistryMedicinal ChemistryDf 1012Bioorganic ChemistryExpensive 7-Azaindole 1Natural SciencesMedicineOrganic ChemistryNew Antitussive DrugChemistryKey Intermediate Df1005PharmacologyPharmaceutical ChemistrySynthetic ChemistryDrug DiscoveryNatural Product Synthesis
An optimised cost-effective synthesis of the new antitussive drug, DF1012, is herewith reported. The new synthetic route to the key intermediate DF1005 is based on the unusual deprotection step of the 1-tert-butyl-3-cyano-7-azaindole intermediate, which can also be regarded as a convenient way for the industrial production of the expensive 7-azaindole 1. The second key intermediate, endo-tropanamine 6, was obtained in high yield by a novel one-pot stereoselective process using a Pd-catalysed reductive amination procedure.
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