1: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h 2: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol View Scheme

propane-1,3-diamine potassium salt

in ammonia 6 h;

1: 1.) NaBH4, BF3-etherate, 2.) 3 N aq. NaOH, 3.) 30percent aq. H2O2 / 1.) THF, 20-25 deg C, 20-25 min, 3.) THF, 30-35 deg C, 2 h 2: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C 3: 66 percent / liquid ammonia / 6 h View Scheme

1: 1.) Mg / 1.) ether, 2.) ether, reflux, 16 h 2: 1.) NaBH4, BF3-etherate, 2.) 3 N aq. NaOH, 3.) 30percent aq. H2O2 / 1.) THF, 20-25 deg C, 20-25 min, 3.) THF, 30-35 deg C, 2 h 3: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C 4: 66 percent / liquid ammonia / 6 h View Scheme

1: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C 2: 66 percent / liquid ammonia / 6 h View Scheme

1: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h 2: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol 3: pyridinium chlorochromate / CH2Cl2 / 7 h View Scheme