ammonia; sodium Reduction;

hydrogenchloride; lithium; ethylamine 1.) THF, -70 deg C, 4 h; -70 deg C -> room temperature, 8 h, 2.) 70 deg C, 14 h; Yield given. Multistep reaction;

1.1: magnesium / tetrahydrofuran 1.2: 8.72 g / copper(I) cyanide; dimethyl sulfide / tetrahydrofuran / 1 h / -20 °C 2.1: 98 percent / tri-n-butylphosphine / tetrahydrofuran / -20 - 20 °C 3.1: n-BuLi / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 2 h / -78 °C 4.1: 89 percent / CuCN*2LiCl / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C 5.1: 78 percent / sodium azide / dimethylformamide / 24 h / 100 °C 6.1: 100 percent / lithium aluminum hydride / diethyl ether / 12 h / 20 °C 7.1: sodium; dibenzo-18-crwn-6 / liquid ammonia; tetrahydrofuran / 0.67 h / -78 °C View Scheme

1.1: 88 percent / CuCN / tetrahydrofuran / 0 °C 2.1: Bu3P / tetrahydrofuran / -20 °C 3.1: BuLi; CuCN*2LiCl / hexamethylphosphoric acid triamide 3.2: tetrahydrofuran / 78 °C 4.1: 78 percent / NaN3 / dimethylformamide / 100 °C 5.1: 100 percent / LiAlH4 / diethyl ether / 0 °C 6.1: Na; NH3 (liq.) View Scheme