sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine in ethanol

1: 98 percent / ammonium sulfate, tert-butyl alcohol, lithium / tetrahydrofuran; liquid ammonia / 2 h 2: 96 percent / pyridine / diethyl ether / 4 h / Ambient temperature View Scheme

ammonium sulfate; lithium; tert-butyl alcohol in tetrahydrofuran; ammonia 2 h;

Multi-step reaction with 3 steps 1: 90 percent / liquid NH3, Li / 2 h2: 85 percent / PBr3, pyridine / diethyl ether / 12 h / Ambient temperature3: 1.) LiNH2, liquid NH3 / 1.) THF, 2 h, 2.) 20 min  

Multi-step reaction with 3 steps 1.1: EtMgBr / tetrahydrofuran / 2 h / 20 °C1.2: cuprous cyanide / hexamethylphosphoric acid triamide; tetrahydrofuran / 50 °C2.1: conc. H2SO4 / CCl4 / Heating3.1: LiAlH4 / tetrahydrofuran