Sulfuric Acid → HCID 59460451, compound

Participants

Reaction Steps

To an ice-cold solution of 2′,3′,5′-tris-O-(tert-butyldimethylsilyl)-8-(3′-methoxycarbonylbiphenyl-4-ylmethylamino)adenosine (0.224 g) in tetrahydrofuran (2.6 mL) was added lithium aluminum hydride (0.013 g) in several portions, and the resulting mixture was stirred at room temperature for 2 hours. Lithium aluminum hydride (0.006 g) was added and stirring was continued for additional 2 hours. Ethyl acetate (1.0 mL), 0.5 mol/L sulfuric acid (1 mL) and water (9 mL) were added sequentially and the whole was extracted with ethyl acetate (35 mL). The organic layer was washed successively with 0.5 mol/L sulfuric acid/water (1/9, 10 mL×2), saturated aqueous sodium hydrogen carbonate (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue (0.173 g) was dissolved in methanol (2.1 mL). Ammonium fluoride (0.468 g) was added, and the resulting mixture was stirred at 60° C. for 21 hours. The reaction mixture was cooled to room temperature. Dichloromethane (10 mL) was added and the insoluble material was filtered out. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on aminopropylated silica gel (eluent: dichloromethane/methanol=10/1 to 6/1) to give the title compound (0.070 g).

Provenance & Evidence