Short synthesis of racemic 5-hydroxy-6-hydroxymethylpiperidin-2-one

A short synthetic sequence to rac -5–hydroxy–6-hydroxymethyl- piperidin-2-one, a useful intermediate in the synthesis of poly- hydroxylated piperidine alkaloids, was based on the hydrobo- ration/oxidation reaction of a 6-furanyl-1,2,3,4-tetrahydropyridine derivative prepared from δ-valerolactam by a Suzuki–Miyaura reac- tion of the corresponding enol phosphate. Two subsequent RuO 2 - catalyzed oxidation steps concluded the synthesis. By this ap- proach, the title lactam was readily obtained in a suitably protected form on the nitrogen and oxygen atoms for its further elaboration . All new compounds were fully characterized by NMR spectroscopy and mass spectrometry.