Triacetoxyperiodinane → 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carbaldehyde

Participants

Reaction Steps

To a solution of 0.092 g (0.246 mmol) of 8-(4-Hydroxymethyl-bicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (Example 15) in 5 ml of CH2Cl2 was added 0.125 g (0.295 mmol) Dess-Martin periodinane. The reaction mixture was stirred at rt until the oxidation was complete. The reaction solution was filtered through a plug of basic alumina, washed with sat'd NaHCO3, brine, and dried over Na2SO4. The CH2Cl2 solution was conc'd in vacuo to give 0.057 g (62% yield) of an off-white solid.(MH+=373.30)

Provenance & Evidence