hydrogen; palladium on activated carbon in ethanol T=45°C; P=2327.23 Torr;

1: With diisobutylaluminium hydride in toluene T=-78 - -60°C; Inert atmosphere; 2: With ammonium hydroxide; acetic acid in water; toluene T=-78 - 5°C; 3: With sodium tetrahydroborate in water; toluene T=5 - 20°C;

1: tert-butoxycarbonyl L-glutamic acidd imethyl ester With ammonium hydroxide; lithium hexamethyldisilazane in tetrahydrofuran T=-78 - -60°C; Inert atmosphere; 2: methyl iodide in tetrahydrofuran T=-70°C; 2 h; Inert atmosphere; 3: With diisobutylaluminium hydride in tetrahydrofuran; toluene T=-70 - -60°C; 1.5 h; Inert atmosphere;

ammonia; hydrogen; benzylamine; palladium 10 on activated carbon in methanol; water P=4137.29 Torr; Parr Shaker; Product distribution / selectivity;

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C 1.2: 5 h / -78 - 20 °C 2.1: hydrogen / palladium 10 on activated carbon / ethanol / 45 °C / 2016.93 Torr View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine / ethyl acetate / 2 h / 20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C 2.2: 5 h / -78 - 20 °C 3.1: hydrogen / palladium 10 on activated carbon / ethanol / 45 °C / 2016.93 Torr View Scheme