hydrogen; palladium on activated charcoal in methanol

1: hydrazinecarboxylic acid tert-butyl ester With sodium hydride in N,N-dimethyl-formamide T=0°C; 2: 1,3-dibromo-propane in N,N-dimethyl-formamide T=0 - 20°C; 3: With water in N,N-dimethyl-formamide T=0°C;

1.1: NaH / dimethylformamide 1.2: 51 percent / dimethylformamide / 16 h / 20 °C 2.1: 95 percent / H2 / Pd/C / methanol View Scheme

1.1: 87 percent / N-methylmorpholine / tetrahydrofuran / 16 h / 20 °C 2.1: NaH / dimethylformamide 2.2: 51 percent / dimethylformamide / 16 h / 20 °C 3.1: 95 percent / H2 / Pd/C / methanol View Scheme

1.1: 78.1 percent / hydrazine monohydrate / propan-2-ol / 0.33 h / 20 °C 2.1: 87 percent / N-methylmorpholine / tetrahydrofuran / 16 h / 20 °C 3.1: NaH / dimethylformamide 3.2: 51 percent / dimethylformamide / 16 h / 20 °C 4.1: 95 percent / H2 / Pd/C / methanol View Scheme