lithium aluminium tetrahydride in diethyl ether 3 h;

lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 7 h; Inert atmosphereCooling with ice;

1: 90 percent / iPr2NEt; DMAP / CH2Cl2 / 16.5 h 2: 49 percent / dimethylformamide / 3 h / 90 °C 3: 93 percent / LiAlH4 / diethyl ether / 3 h View Scheme

1: 1.) diphenylphosphoryl azide, Et3N 2: H2 / Pd View Scheme

1: N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 7 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme

T=180 - 200°C;