sodium hydroxide; Ni(OAr)2*4H2O; hydrogen; ethylenediamine in ethanol Ambient temperature;

1: 90 percent / NaB4, aq. NaOH, Ni(OAr)2*4H2O, ethylenediamine, H2 / ethanol / Ambient temperature 2: 89 percent / LiAlH4 / diethyl ether / 2 h / 0 °C 3: 80 percent / pyridine / 12 h / Ambient temperature View Scheme

1: 90 percent / NaB4, aq. NaOH, Ni(OAr)2*4H2O, ethylenediamine, H2 / ethanol / Ambient temperature 2: 89 percent / LiAlH4 / diethyl ether / 2 h / 0 °C View Scheme

Multi-step reaction with 4 steps 1: 1.) BuLi / 1.) THF, HMPT, hexane, 1 h, 2.) THF, HMPT, hexane, overnight2: 77 percent / PBr3, pyridine / diethyl ether / 1.) -15 deg C, 2 h, 2.) room temp., 3 h, then 30 deg C, 45 min3: 1.) Mg / 1.) Et2O, 2.) Et2O, -15 deg C, 0.5 h, -15 to 0 deg C, 0.5 h4: 68 percent / propionic acid / 2 h / 136 - 139 °C