Water → HCID 57867403, compound

Participants

Reaction Steps

To a stirred solution of ((2R,4R)-3-acetoxy-5-(6-chloro-9H-purin-9-yl)-4-fluoro-3,4-dimethyl-tetrahydrofuran-2-yl)methyl benzoate (about 0.50 g, 1.08 mmol) in ethanol (about 5 ml) was added cyclohexylamine (about 1.48 ml, 12.9 mmol) and refluxed for about 30 minutes. Completion of the reaction mixture monitored by thin-layer chromatography, water added to the reaction mixture and the aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine and dried over sodium sulphate. Concentration under reduced pressure and purification by silica gel column chromatography using 6% methanol in dichloromethane as eluent furnished title compound (0.42 g) as a colorless solid. Yield: 74%; 1H-NMR: 1H NMR (300 MHz, CDCl3): δ 8.38 (s, 1H), 8.06-7.96 (m, 3H), 7.58-7.42 (m, 3H), 6.54 (d, 1H, J=23.1 Hz), 5.77 (d, 1H, J=8.1 Hz), 4.83-4.78 (m, 2H), 4.48-4.41 (m, 1H), 2.16 (s, 3H), 2.13-1.77 (m, 14H), 1.45 (d, 3H, J=23.1 Hz); ES Mass: [M+1]+ 512 (20%), [M+Na] 534 (100%); IR cm−: 3414, 2926, 2854, 1724, 1618, 1229, 1063, 950, 712; HPLC: 98%.

Provenance & Evidence