Tert-Butyl nitrite → HCID 86607294, compound

Participants

Reaction Steps

To a solution of (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)tetrahydrofuran-3-yl acetate (2.00 g, 4.91 mmol) in dibromomethane (98.2 mL) were added trimethylsilylbromide (0.717 mL, 5.55 mmol) then t-butylnitrite (3.98 mL, 33.44 mmol). The reaction mixture was stirred at room temperature for approximately 3 hours before being slowly poured into a 1:1 mixture of saturated NaHCO3:CH2Cl2. The organics were washed with water then brine. After drying over Na2SO4, the solvent was removed in vacuo. The crude product was purified by flash chromatography (0% to 30% EtOAc/Hex) to obtain the title compound as a yellow oil (1.26 g, 55%).

Provenance & Evidence