Tert-Butyl nitrite → Ammonia

Participants

Reaction Steps

It is further known in the literature that 2-aminoadenosine-2',3',5'-tri-O-acetate can be converted with tert-butyl nitrite or sodium nitrite in 50% HF/pyridine to a mixture of the corresponding 2-fluoroadenosine-2',3',5'-tri-O-acetate and 2,6-difluoro-nebularine-2',3',5'-tri-O-acetate, which, with dry ammonia gas in 1,2-dimethoxy-ethane, yields pure 2-fluoroadenosine-2',3',5'-tri-O-acetate in about a 60% yield (M. J. Robins, B. Uznanski, Can. J. Chem. 59, 2608 (1961)). A drawback of this process, however, is that because of the obtained mixture, another reaction step is necessary to obtain the pure 2-fluoronucleoside.

Provenance & Evidence