Pyridine → (1S,2R,4R)-4-(6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol

Participants

Reaction Steps

To a solution of 6-chloro-9-[(6aR,8R,9aS)-2,2,4,4-tetraisopropylhexahydrocyclopenta[f][1,3,5,2,4]trioxadisilocin-8-yl]-9H-purine (0.518 g, 1.0 mmol) in THF/pyridine (5.2 mL, 1:1) was added hydrofluoric acid in pyridine (0.381 mL, 15.2 mmol). The reaction was stirred for 14 h then quenched with saturated aq NaHCO3 and concentrated under reduced pressure. The residue was dissolved in 10% solution of MeOH/DCM, filtered, the organic layer was concentrated and the residue purified by flash chromatography (0 to 10% MeOH/DCM to afford the title compound (0.171 g, 63%).

Provenance & Evidence