nitrogen in methanol; N,N-dimethyl-formamide

in N,N-dimethyl-formamide T=60 - 80°C; 22 h;

in N,N-dimethyl-formamide T=80°C; 24 h;

T=80°C; Reagent/catalystTimeTemperature;

1: chlorotrimethylsilane / 36 h / Heating 2: 93 percent / H2 / Pd/C / methanol / 760.05 Torr View Scheme

1: 84 percent / TMSCl / 22 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C / 1034.3 - 2585.74 Torr 3: 92 percent / NaBH(OAc)3 / acetic acid / 18 h / 50 °C View Scheme

1.1: 84 percent / TMSCl / 22 h / Heating 2.1: 100 percent / H2 / Pd/C / methanol / 20 °C / 1034.3 - 2585.74 Torr 3.1: 83 percent / NaBH(OAc)3 / acetic acid / 19 h / 20 - 50 °C 4.1: 98 percent / H2 / Pd/C / methanol / 20 h / 2585.74 Torr 5.1: 97 percent / K2CO3 / dimethylformamide / 5 h / 20 - 50 °C 6.1: HCl gas / acetonitrile / 0.5 h / 0 - 20 °C 6.2: acetonitrile / 2 h / -10 - 0 °C 6.3: 86.5 percent / acetonitrile / 1 h / -10 - 0 °C 7.1: 75 percent / t-BuOK / tetrahydrofuran / -5 - 45 °C View Scheme

1: 84 percent / TMSCl / 22 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C / 1034.3 - 2585.74 Torr 3: 91 percent / NaBH(OAc)3 / acetic acid / 2.5 h / 20 - 100 °C View Scheme

1: 84 percent / TMSCl / 22 h / Heating 2: 100 percent / H2 / Pd/C / methanol / 20 °C / 1034.3 - 2585.74 Torr 3: 83 percent / NaBH(OAc)3 / acetic acid / 19 h / 20 - 50 °C 4: 98 percent / H2 / Pd/C / methanol / 20 h / 2585.74 Torr View Scheme

p-toluenesulfonic acid monohydrate T=23 - 68°C; 3 h; Inert atmosphere; Reagent/catalystTimeTemperature;