Tert-Butyl nitrite → 2'-Deoxy-2-fluoroadenosine

Participants

Reaction Conditions

Reaction Steps

DAPD (2 g, 7.5 mmol) was suspended in 170 mL dichloroethane/DMSO (4:1) and cooled to 0° C. under an inert atmosphere. To this is added antimony trifluoride (1.88 g, 10.5 mmol) and tert-butyl nitrite (1.85 ml, 1.6 g, 15.5 mmol) followed by stirring while allowing the reaction to warm to room temperature. Analysis of the reaction mixture by HPLC [Novapak C-18; 5% acetonitrile/water, 0.1M TEA, pH 7 with acetic acid] revealed a new peak which eluted at 6.4 min, indicating the synthesis of 2-fluoro-2′-deoxyadenosine with concomitant loss of starting material. The reaction was stirred overnight and quenched with triethylamine. The conversion to product by HPLC was 8%.

Provenance & Evidence