1: With hydrogenchloride in ethyl acetate 2 h; 2: With potassium carbonate in diethyl ether; water

ammonium formate; palladium on activated charcoal in methanol

1: With ammonia; lithium in tetrahydrofuran T=-78°C; 4.5 h; 2: With ammonium chloride in tetrahydrofuran T=-78 - 20°C; 16 h;

borane-THF in tetrahydrofuran T=0°C; 3.5 h; Inert atmosphereReflux;

1.1: 85 percent / triethylamine / CH2Cl2 / 3 h / 0 - 20 °C 2.1: 95 percent / di(tricyclohexylphosphine)(benzylidene)ruthenium dichloride / CH2Cl2 / 15 h / 20 °C 3.1: 87 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 15 h / 110 °C 4.1: 93 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 5.1: lithium; NH3 / tetrahydrofuran / 4.5 h / -78 °C 5.2: 90 percent / NH4Cl / tetrahydrofuran / 16 h / -78 - 20 °C View Scheme

1.1: 93 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 2.1: lithium; NH3 / tetrahydrofuran / 4.5 h / -78 °C 2.2: 90 percent / NH4Cl / tetrahydrofuran / 16 h / -78 - 20 °C View Scheme

1.1: 87 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 15 h / 110 °C 2.1: 93 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 3.1: lithium; NH3 / tetrahydrofuran / 4.5 h / -78 °C 3.2: 90 percent / NH4Cl / tetrahydrofuran / 16 h / -78 - 20 °C View Scheme

1.1: 95 percent / di(tricyclohexylphosphine)(benzylidene)ruthenium dichloride / CH2Cl2 / 15 h / 20 °C 2.1: 87 percent / Pd(OAc)2; triphenylphosphine; K2CO3 / dimethylformamide / 15 h / 110 °C 3.1: 93 percent / H2 / Pd/C / ethanol / 15 h / 20 °C 4.1: lithium; NH3 / tetrahydrofuran / 4.5 h / -78 °C 4.2: 90 percent / NH4Cl / tetrahydrofuran / 16 h / -78 - 20 °C View Scheme

1: HCO2NH4 / Pd/C / methanol / 4 h / Heating 2: aq. HCl / methanol / Heating View Scheme

1: 1.) NaHCO3; 2.) t-BuOK / 1.) MeOH; 2.) t-BuOH 2: HCOONH4, 10percent Pd-C / methanol View Scheme