Tert-Butyl nitrite → HCID 86607300, compound

Participants

Reaction Steps

(2R,3S,4R,5R)-2-(6Amino-9H-purin-9-yl)-5-{[(triisopropylsilyl)oxy]methyl}-tetrahydrofuran-3,4-diyl diacetate (0.605 g, 1.19 mmol) was dissolved in dibromomethane (24 mL). Trimethylsilyl bromide (0.17 mL, 1.35 mmol) was added dropwise followed by tert-butylnitrite (0.97 mL, 8.12 mmol). The orange solution was stirred for 2.5 hours then slowly poured into a 1:1 mixture of saturated sodium bicarbonate and dichloromethane and extracted. The pale yellow organic layer was washed with water and brine, dried (Na2SO4), filtered and concentrated. The yellow solid was purified by flash chromatography eluting with 25% ethyl acetate/hexanes to give the title compound as a yellow solid (0.402 g, 52%).

Provenance & Evidence