Réaction #531896

Équation de réaction

4-(benzyl-tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester

hydrogen

→

4-(tert-butoxycarbonylmethyl-amino)-cyclohexanecarboxylic acid tert-butyl ester

Rendement 104.3%

Solvants

EtOH

Conditions de réaction

Traitement

1. 1
   FiltrationThe mixture is then filtered though celite
2. 2
   LavageThe celite is washed with MeOH (50 mL)
3. 3
   ConcentrationThe filtrated is concentrated

Mode opératoire

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).

Source