Ethanol → tert-butyl N-((4-(aminomethyl)cyclohexyl)methyl)carbamate

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To a solution of [4-(tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester (11.00 g, 32 mmol) dissolved in 2:1 CHCl3:EtOH at room temperature was added 4.0 M HCl/dioxane (16.1 mL). The mixture was stirred at room temperature for 4 h then concentrated in vacuo to provide a crude white solid. The crude material was purified by silica gel chromatography using a gradient elution of 10-50% (2% NH4OH, 18% MeOH, 80% CH2Cl2)/CH2Cl2. The product-containing fractions were combined and concentrated in vacuo to provide (4-aminomethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester as a white powder 3.62 g, 47%, m/z calculated for C13H26N2O2: 242.4, found: 243.3 (M+H)+.

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