Hydrochloric Acid → HCID 178510902, compound

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Reaction Steps

To a solution of cyclopentylidene-(2-trityl-2H-tetrazol-5-yl)-acetonitrile (2.05 g, 4.91 mmol) in 50 mL MeOH:THF (1:1) was added PtO2 (0.2 g), concentrated HCl (1.49 g), and the mixture was hydrogenated in a Parr shaker at 48 psi for 8 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), followed by a second column using the same conditions, provided 0.54 g (61%) of 2-cyclopentyl-2-(1H-tetrazol-5-yl)-ethylamine as a colorless solid. 1H NMR (D2O) δ 3.22 (m, 2H, —CH2NH2), 3.06 (m, 1H, —CHCH2NH2), 1.99 (m, 1H, —CHCHCH2NH2), 1.72 (m, 1H), 1.03-1.38 (m, 6H), 0.87 (m, 1H). 13C NMR (CD3OD) □ 161.11, 42.78, 42.56, 40.48, 30.61, 30.11, 24.96, 24.53. LRMS: m/z 180.1 (M−1). Anal. Calc'd for C8H15N5: C, 53.02; H, 8.34; N, 38.64. Found: C, 51.59; H, 8.18; N, 37.96.

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