The complex chiral 3,4-disubstituted piperidine 61, invented by Merck scientists, is an intermediate used to produce a potent and selective inhibitor of renin with a suitable profile for further clinical development. Although the process-scale synthesis of 61 allowed for Kg-scale production of this compound, the overall route relies exclusively on polar bond disconnections and precious metal catalysis for both the piperidine subunit and aryl side chain. For the aryl fragment 57, a four-step reaction process is employed, two of which involve precious metal catalyzed coupling and hydrogenation. In contrast, dibromobenzoic acid 55 can be subjected to amide bond formation with cyclopropyl amine followed by mono-selective Ni/Ag-electrocatalytic decarboxylative arylation 7 to furnish the same arene 57, which can then be subjected to boranemediated reduction to afford benzyl amine 58. The process-scale route to the piperidine subunit starts from commercially available benzyl-protected β-keto ester 62 and traverses a total of 10 reaction steps to obtain the target molecule, only three of which make skeletal bonds (C-C and C-N). These steps include Pd-catalyzed hydrogenation, borylation, and Suzuki coupling, along with a Ru-catalyzed asymmetric hydrogenation. These precious metal catalyzed reactions significantly increase cost and require a high-pressure hydrogenation. In stark contrast, the same product can be obtained through the amide coupling of 18 with benzylic amine 58, and an Appel reaction to generate the alkyl iodide which subsequently is coupled to iodopyridone 60 under Ag/Nielectrocatalysis. The chemoselectivity of the pivotal cross-coupling is notable as the aryl bromide is untouched. In this five-step sequence, four of the steps are skeletal bond forming (C-C, C-O, C-N) and precious metals are completely removed. A conservative estimate of cost savings just based on the raw cost of metals employed (not including ligand cost) is profound and differs by three orders of magnitude (ca. $1 for Ni vs. ca. $1765 for the Pd, Pt, and Ru). Overall, the route outlined above is considerably shorter (5 steps, 8 steps total) than the current process route (10, 14