Ethyl Acetate → 3-(2,6-Dichloro-purin-9-yl)-5-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopentane-1,2-diol

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Reaction Steps

A solution of 2,6-dichloro-9-[(1R,4S)-4-(4-ethyl-[1,2,3]triazol-1-yl)-cyclopent-2-enyl]-9H-purine (1.442 g, 4.12 mmol) in EtOAc (15 mL) and MeCN (15 mL) is treated with a solution of ruthenium trichloride (0.120 g, 0.58 mmol) and sodium periodate (1.32 g, 6.18 mmol) in water (5 mL). The reaction mixture is stirred vigorously for 6 hours and then treated with sodium metabisulfite (saturated aqueous solution, 25 mL) and then stirred overnight. The resulting mixture is partitioned between water and EtOAc and the aqueous portion is extracted with EtOAc. The combined organic portions are washed with water, dried (MgSO4) and concentrated in vacuo. The crude product is purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane to afford the title compound as an oil orange solid. (MH+ 350).

Provenance & Evidence