HCID 69516187, compound → HCID 178509357, compound

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Reaction Steps

To a solution of the 2-cyclohexyl-1-(2-trityl-2H-tetrazol-5-yl)-cyclopropanecarbonitrile (1.10 g, 2.39 mmol) in 50 mL 2.0M NH3 in EtOH was added RaNi (1.4 g), and the mixture was hydrogenated in a Parr shaker at 48 psi for 60 h. The mixture was filtered and concentrated. Flash chromatography of the residue on silica gel (0.25:1.25:3.5 conc. NH4OH (aq):MeOH:CH2Cl2) furnished 0.19 g (36%) of C-[2-cyclohexyl-1-(1H-tetrazol-5-yl)-cyclopropyl]-methylamine as a colorless solid. 1H NMR (CD3OD) δ 3.97 (d, J=13.2 Hz, 1H, —CH2NH2), 2.96 (d, J=13.2 Hz, 1H, —CH2NH2), 1.87 (m, 1H), 1.77 (m, 1H), 1.68 (m, 2H), 1.47 (m, 1H), 1.38 (m, 1H), 1.12-1.31 (m, 6H), 1.07 (m, 1H), 0.91 (dd, J=4.6, 6.6 Hz, 1H, cyclopropyl —CHH). LRMS: m/z 220.2 (M−1). Anal. Calc'd for C11H19N5: C, 59.70; H, 8.65; N, 31.65. Found: C, 58.39; H, 8.54; N, 31.20.

Provenance & Evidence