1.1: 92 percent / lithium 3-aminopropanamide; potassium tert-butoxide; propane-1,3-diamine / 0.5 h / 20 °C 2.1: DMPU; n-BuLi / hexane; tetrahydrofuran / -20 - 0 °C 2.2: 54 percent / tetrahydrofuran; hexane / 0 - 20 °C 3.1: 95 percent / H2; quinoline / Lindlar's catalyst / benzene / 2 h / 20 °C / 760 Torr View Scheme

lithium aluminium tetrahydride in diethylene glycol dimethyl ether T=120 - 125°C; 22 h;

1: LiAlH4 / tetrahydrofuran; bis-(2-methoxy-ethyl) ether / 36 h / 140 °C 2: 1.1 g / pyridine / 24 h / Ambient temperature View Scheme

toluene-4-sulfonic acid in methanol T=60 - 65°C; 4 h;

1: 1) Li, FeCl3, NH3 / 1) -35 deg C, 1 h, 2) THP, DMSO, -40 deg C, 2 h 2: 2.9 g / TsOH / methanol; H2O / 20 h View Scheme

1: 87 percent / ethylenediamine 2: 74 percent / n-BuLi, DMPU / tetrahydrofuran; hexane / 1.) 0 deg C, 2 h, 2.) room temperature, overnight 3: 99 percent / p-TsOH / methanol / 4 h / 60 - 65 °C View Scheme

1: With potassium tert-butylate; lithium (3-aminopropyl)amide; 1,3-diamino-propane 2: With water