A novel asymmetric synthesis of cinacalcet hydrochloride

• Veera R. Arava,
• Laxminarasimhulu Gorentla and
• Pramod K. Dubey

Beilstein J. Org. Chem. 2012, 8, 1366–1373, doi:10.3762/bjoc.8.158

• )-tert-butanesulfinamide and regioselective N-alkylation of the naphthyl ethyl sulfinamide intermediate is described. Keywords: asymmetric synthesis; (R)-tert-butanesulfinamide; cinacalcet hydrochloride; naphthyl ethyl sulfinamide; regioselective N-alkylation; Introduction Cinacalcet hydrochloride

• alcohol intermediate 12 from 10. Synthesis of bromo 5 and iodo 6 derivatives. Regioselective N-alkylation of naphthyl ethyl sulfinamide 4a. Acid hydrolysis of N-tert-butanesulfinyl group in 7. Screening of reduction conditions (9→10). Conditions for regioselective N-alkylation of naphthylethylsulfinamide