(2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate → (4S,2R,3R,5R)-2-[2-(aminomethyl)-6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

Participants

Reaction Steps

To a solution of (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxy-methyl)-5-[2-cyano-6-(cyclopentylamino)purin-9-yl]oxolan-3-yl acetate (0.3 g) in methanol was added Raney nickel, and the mixture was stirred under hydrogen at 40 psi for 2 hours at room temperature. The catalyst was filtered off through celite, washed with methanol, and solvent removed from the filtrate under reduced pressure. The residue was crystallized from a mixture of methanol and hexane, to provide (4S,2R,3R,5R)-2-[2-(aminomethyl)-6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol. B. Preparation of a Compound of Formula (6) varying R1 and Y

Provenance & Evidence