Triacetoxyperiodinane → (R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-N-[(S)-1-(5-trifluoromethyl-1,2,4-oxadiazole-3-carbonyl)-propyl]-butyramide

Participants

Reaction Steps

A solution of (R)-2-Cyclohexylmethyl-N-{(S)-1-[hydroxy-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-4-morpholin-4-yl-4-oxo-butyramide (324 mg, 0.661 mmol) in methylene chloride (10 ml) was treated with Dess Martin periodinane (308 mg, 0.726 mmol) and stirred at room temperature for 90 minutes. The reaction mixture was washed with an aqueous solution of Na2S2O3 (0.26M), saturated aqueous bicarbonate solution and water, dried over Na2SO4 and the solvent evaporated under reduced pressure. The crude was purified by flash chromatography eluting with a mixture of ethyl acetate and heptane to give (R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-N-[(S)-1-(5-trifluoromethyl-1,2,4-oxadiazole-3-carbonyl)-propyl]-butyramide as an off white solid (10 mg).

Provenance & Evidence