Cyclohexene → Doxifluridine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a suspension of 10 g (0.026 m) of 5′-deoxy-5′-iodo-5-fluoro uridine, obtained as described in Example 2, step A, in 100 ml of n-butanol, 6 ml of cyclohexene (0.06 m) and 14 ml (0.1 m) of triethylamine are added. The mixture is heated to 60° C. in order to achieve a complete solubilization, then 1.5 g of 5% Pd/C are added thereinto. The suspension is heated at 80° C. for 5 hours, filtered at the same temperature by washing with hot n-butanol and concentrated under vacuum until a residue is obtained, which crystallizes with a mixture of 60 ml of ethanol and 40 ml of isopropanol. Thus, 4.5 g of 5′-deoxy-5-fluorouridine are obtained. M.p.=188÷189° C., purity (HPLC)=99.87% and [α]D=18.35° (c=0.42, H2O).

Herkunft & Nachweise