lithium borohydride in tetrahydrofuran T=0 - 20°C; Inert atmosphere;

1.1: lithium borohydride / tetrahydrofuran / 16 h / 0 - 20 °C 1.2: 0 °C 2.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 48 h / 20 °C 3.1: hydrogenchloride / methanol / 20 °C View Scheme

1: sodium amide / tetrahydrofuran / 2 h / -33 °C / |Inert atmosphere 2: dichloromethane / 3.5 h / 0 - 20 °C / |Inert atmosphere 3: triethylamine / acetic acid / 2 h / |Reflux; |Inert atmosphere View Scheme

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran 1.2: tetrahydrofuran 2.1: trifluoroacetic acid / CH2Cl2 2.2: toluene / Heating 3.1: 4-(dimethylamino)pyridine / acetonitrile 4.1: lithium triethylborohydride / tetrahydrofuran / 0.67 h / -78 °C 4.2: H2O2 / tetrahydrofuran / 0.33 h / 0 °C 4.3: 89 percent / triethylsilane; BF3*OEt2 / CH2Cl2 / 3 h / -78 °C 5.1: 86 percent / NaOH / methanol; H2O / 6 h / 20 °C View Scheme

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;