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 CH2Br2 (98.2 mL) was added TMSBr (0.717 mL, 5.55 mmol) and t-butylnitrite (3.98 mL, 33.4 mmol). The reaction mixture was stirred at r.t. for 3 hours then slowly poured into 50 mL of a 1:1 mixture of saturated aq NaHCO3:CH2Cl2. The organic layer was washed with water (50 mL), brine (50 mL), dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 30% EtOAc/hexanes) to obtain the title compound as a yellow oil (1.26 g, 55%).

Provenance & Evidence