Cyclopropylamine → (2R,3R,4S,5R)-2-[5,6-dichloro-2-(cyclopropylamino)benzimidazol-1-yl]-5-methyl-tetrahydrofuran-3,4-diol

Participants

Reaction Steps

Following General Procedure V, cyclopropyl amine (Aldrich, 5 mL, 71.28 mmol), and 2-bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole (250 mg, 0.65 mmol) reacted for 92 h. Purification on a silica gel column with 1:15 methanol:CH2Cl2 gave the title compound (120 mg, 0.33 mmol, 52%); MS (El): m/z (rel. intensity) 358 (0.08, M+); 1H NMR (DMSO-d6) δ7.48 (s, 1H, Ar—H), 7.35 (s, 1H, Ar—H), 7.13 (d, 1H, NH, J=2.0 Hz), 5.61 (d,1H, CH, J=6.6 Hz), 5.25 (m, 2H, 2 overlapping OH), 4.36 (m,1H, CH), 3.88 (m, 1H, CH), 3.79 (m, 1H, CH), 2.76 (m, 1H, CH), 1.36 (d, 3H, CH3, J=6.3 Hz), 0.70 (m, 2H, CH2), 0.53 (m, 2H, CH2).

Provenance & Evidence