Triacetoxyperiodinane → 4-Oxo-2-benzylsulfonyl-methyl-4-piperidin-1-yl-n-[1-(5-pyridin-4-yl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-butyramide

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Reaction Steps

This amide was treated with Dess-Martin periodinane (222.7 mg, 0.45 mmol) at room temperature. After stirring for 1 hour, 5 mls of saturated Na2SO3—NaHCO3 were added. After a further 0.5 hours, the reaction mixture was extracted with ethyl acetate, washed with brine, dried with MgSO4 and concentrated. The residue was purified with silica gel column chromatography to yield 78 mg of 4-oxo-2-benzylsulfonyl-methyl-4-piperidin-1-yl-N-[1-(5-pyridin-4-yl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-butyramide; H1 NMR(DMSO-d): 9.0–8.85(3H, m), 8.1–8(2H, m), 7.44–7.3(5H, m), 5–4.9(1H, m), 4.5–4.3(2H, m), 3.6–3.2(11H, m), 3.15–3.05(1H, m), 2.7–2.5(1H, m), 2.05–1.9(1H, m), 1.8–1.7(1H, m), 0.96(3H, t); MS: 568.6(M−1), 570.6(M+1).

Provenance & Evidence