Water → HCID 57308030, compound

Participants

Reaction Steps

(4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)1-cyclopentene-1-methanol (Part b, 501 mg, 1.89 mmol), N-methylmorpholine N-oxide (60% aqueous solution, Aldrich, 0.33 mL 1.89 mmol), osmium tetroxide (2.5% in t-butyl alcohol Aldrich, 0.47 mL), and t-butyl alcohol (12 mL) were heated at 60° C. for 1.5 hours. Volatiles were evaporated and the residual solids were chromatographed on silica gel. Title compound was eluted with 10% methanol chloroform as tan solid (210 mg) and resolidified from absolute ethanol to give white powder, m.p. 217-219° C.; mass spectrum (CI/CH4): 302, 300 (M+1), 172, 170 (B+H); 1H-NMR (DMSO-d6)δ: 8.29 (s, 1, purine CH), 6.9 (br s, 2, NH2), 5.15-4.90 (m, 1, NCH), 4.80 (d, J=3.9 Hz) overlapping 4.78 (t, J=3.5 Hz, total 2, 2 OH), 4.30 (s) overlapping 4.3-4.2 (m, total 2, OH and OCH), 3.45-3.35 (m, overlapping water, CH2OH), 2.25-2.05 (m, 4, 2 CH2).

Provenance & Evidence