Cyclopentylamine → (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate

Participants

Reaction Steps

To a solution of (2R,3R,4R,5R)-4-acetyloxy-5-(acetyloxymethyl)-2-(6-chloro-2-iodopurin-9-yl)oxolan-3-yl acetate (1.15 g, 2.13 mmol) in N,N-dimethylformamide (20 ml) was added cyclopentylamine (0.42 ml, 4.26 mmol) and diisopropylethylamine (10 ml), and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue chromatographed on a silica gel column, eluting with a mixture of 40% ethanol/60% hexane, to provide (2R,3R,4R,5R)-4-acetyloxy-2-(acetyloxymethyl)-5-[6-(cyclopentylamino)-2-iodopurin-9-yl]oxolan-3-yl acetate (0.9 g), a compound of formula (4).

Provenance & Evidence