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Beilstein J. Org. Chem. 2012, 8, 1366–1373, doi:10.3762/bjoc.8.158
Graphical Abstract
Figure 1: Cinalcet hydrochloride (CNC·HCl, 1).
Scheme 1: Asymmetric synthesis of 1.
Scheme 2: Synthesis of the intermediates 5 and 6 from 8.
Scheme 3: Asymmetric synthesis of naphthylethylsulfinamide 4.
Scheme 4: Conversion of 8 to 10.
Scheme 5: Synthesis of alcohol intermediate 12 from 10.
Scheme 6: Synthesis of bromo 5 and iodo 6 derivatives.
Scheme 7: Regioselective N-alkylation of naphthyl ethyl sulfinamide 4a.
Scheme 8: Acid hydrolysis of N-tert-butanesulfinyl group in 7.