Triethylamine → HCID 44343895, compound

Participants

Reaction Conditions

Reaction Steps

Trans-2-hydroxycyclopentylamine (0.35 g, 3.46 mmol)(prepared by reaction of cyclopentene oxide with ammonia in a sealed vessel: see example 11) was reacted with 6-chloropurine riboside (i.e. 9-β-D-ribofuranosyl-9H-purine) (0.5 g, 1.7 mmol) in dioxan (30 ml) in the presence of triethylamine (0.93 g, 9 mmol). The reaction mixture was heated at 100° C. for 70 h, cooled and evaporated. The resultant residue was purified by flash chromatography eluting with a mixture of ethyl acetate and methanol (19:1). The fractions found to contain the highest amounts of N-[(1R, trans)-2-hydroxycyclopentyl]adenosine following HPLC examination, were combined and evaporated to a solid (0.17 g). Recrystallisation from methanol provided the pure N-[(1R, trans)-2-hydroxycyclopentyl]adenosine (0.11 g, 18%) mp 233°-235° C. 1H NMR (DMSO-d6)δ 1.43-2.12 (6H, 4m, --CH2CH2CH2 --), 3.52-3.59 (1H, m, H-5'a), 3.54-3.71 (1H, m, H-5'b), 3.97 (1H, q, H-4'), 4.07 (1H, br, --C HOH) 4.15 (1H, q, H-3'), 4.61 (1H, q, H-2'), 4.87, 5.21, 5.41-5.47 (4H, d & 3m, OH groups), 5.89 (1H, d, H-1'), 7.75 (1H, br d, --NH), 8.21 and 8.37 (H-2 and H-8).

Provenance & Evidence