O-(2-phenylethyl)hydroxylamine;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 3.2 mmol), O-(2-phenylethyl)hydroxylamine hydrochloride (0.70 g, 4.0 mmol) and diisopropylethylamine (0.95 g, 7.4 mmol) were dissolved in 1,4-dioxan (40 ml) and heated at reflux for 3 days. After cooling the reaction mixture was diluted with dichloromethane (50 ml) and washed with water (2×30 ml). The organic phase was dried (MgSO4). Flash chromatography on a silica gel column, eluting with heptane/ethyl acetate (1/1) gave the desired product as a foam (1.54 g, 66%), 1H NMR (DMSO-d6)γ 3.05 (2H, t, --OCH2 --), 4.19 (2H, t,--CH2Ph), 4.70 (1H, dd, H-5'a), 4.80 (1H, dd, H-5'b), 4.90 (1H, dd, H-4'), 5.22 (1H, t, H-3'), 6.39 (1H, t, H-2'), 6.59 (1H, d, H-1'), 8.51 (1H, s H-8). heated at reflux for 3 days After cooling the reaction mixture washed with water (2×30 ml) The organic phase was dried (MgSO4) Flash chromatography on a silica gel column, eluting with heptane/ethyl acetate (1/1)