4-(Benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester → 4-(Tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester

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To a solution of 4-(benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester (300 mg, 0.7433 mmol) in EtOH (10 mL) is added 10% Pd/C (wet) (40 mg). The mixture stirs under a blanket of hydrogen gas at atmospheric pressure for 12 h. The mixture is then filtered though celite. The celite is washed with MeOH (50 mL). The filtrated is concentrated to afford 243 mg of 4-(tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester. 1H NMR (400 MHz, DMSO-D6) δ ppm 0.98 (m, 2 H), 1.25 (m, 2 H), 1.36 (m, 9 H), 1.41 (m, 9 H), 1.81 (m, 4 H), 2.05 (m, 1 H), 2.28 (m, 1 H), 3.20 (m, 2 H).

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