Triacetoxyperiodinane → 1-(3-((1-(Quinolin-2-yl)piperidin-4-yl)oxy)pyrazin-2-yl)piperidin-4-one

Participants

Reaction Steps

1-(3-((1-(quinolin-2-yl)piperidin-4-yl)oxy)pyrazin-2-yl)piperidin-4-ol (see Example 1.1; 0.10 g, 0.25 mmol) was dissolved in anhydrous CH2Cl2 (10 mL), treated with Dess-Martin periodinane (DMP) (200 mg, 0.50 mmol, 2.0 equiv) and stirred at RT until complete conversion. The organic layer was washed with an aqueous solution of NaHCO3/Na2S2O3 (3×10 mL)), dried over Na2SO4, filtered and evaporated. The resulting residue was purified by flash chromatography on silica gel (20% to 40% EtOAc in petroleum ether) to give 1-(3-((1-(quinolin-2-yl)piperidin-4-yl)oxy)pyrazin-2-yl)piperidin-4-one (0.084 g, 0.20 mmol, 83% yield) as a white solid. ESI-MS (M+1): 404 calc. for C23H25N5O2 403.

Provenance & Evidence