Sodium Iodide → [(3aR,4R,6R,6aS)-6-(6-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate

Participants

Reaction Conditions

Reaction Steps

To a solution of [(3aR,4R,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methyl acetate (185 mg, 0.45 mmol) in 2-butanone (8 mL) at 0° C. was added NaI (1.36 g, 9.08 mmol) followed by trifluoroacetic acid (174.8 μL, 2.27 mmol). The reaction was stirred for 3 hours at 0° C., quenched with saturated aq NaHCO3 and extracted with DCM. The organic phase was concentrated and the residue was purified by flash chromatography (0 to 100% EtOAc/DCM) to obtain the title compound (140 mg, 67%).

Provenance & Evidence