Ethyl isonipecotate (I) was protected as the N-Boc derivative (II) employing di-tert-butyl dicarbonate. Sulfenylation of the lithium enolate of ester (II) with the disulfide (IV), generated from the oxidation of 4-fluorothiophenol (III), furnished the phenylsulfanyl derivative (V). Thioether (V) was then oxidized to the corresponding sulfone (VI) by means of meta-chloroperbenzoic acid. After acidic Boc group cleavage in (VI), the resultant piperidine (VII) was alkylated with propargyl bromide (VIII) to produce the N-propargyl piperidine (IX).

Displacement of the 4-fluoro group of (IX) with thiophenol (X) in the presence of K2CO3 led to the diaryl sulfide (XI). Acid (XII), prepared by alkaline hydrolysis of ester (XI), was then coupled to O-tetrahydropyranyl hydroxylamine (XIII) by means of EDC to furnish (XIV). Finally, acidic cleavage of the tetrahydropyranyl moiety produced the corresponding hydroxamic acid.