lithium aluminium tetrahydride; chloro-trimethyl-silane in tetrahydrofuran T=-50 - 20°C;

1.1: NaH / dimethylformamide / 1 h / 60 °C 1.2: dimethylformamide / 16 h / 60 °C 2.1: 5.87 g / NH3 / methanol / 14 h / 20 °C 3.1: sodium tert-butoxide / dimethylformamide / 0.67 h / 20 °C 3.2: 27 percent / dimethylformamide / 72 h / 20 °C 4.1: 78 percent / TMSCl; LiAlH4 / tetrahydrofuran / -50 - 20 °C View Scheme

1.1: sodium tert-butoxide / dimethylformamide / 0.67 h / 20 °C 1.2: 27 percent / dimethylformamide / 72 h / 20 °C 2.1: 78 percent / TMSCl; LiAlH4 / tetrahydrofuran / -50 - 20 °C View Scheme