sodium hydroxide in methanol 18 h; Ambient temperature;

1: 90 percent / PCl5 / xylene / 0.5 h / 90 °C 2: 95 percent / H2, sodium acetate / 5percent Pd/C / acetic acid / 0.5 h / 760 Torr / Ambient temperature 3: 90 percent / sodium azide / dimethylsulfoxide / 3 h / 80 °C 4: 96 percent / Bu4NBr, KOH / tetrahydrofuran / 1.5 h / Ambient temperature 5: 93 percent / H2 / 10percent Pd/C / ethanol / 1.5 h / 2280 Torr / Ambient temperature 7: 89 percent / aq. NaOH / methanol / 2 h / Ambient temperature 8: 25 percent / sodium cyanoborohydride / acetic acid; methanol / Ambient temperature View Scheme

1: 95 percent / H2, sodium acetate / 5percent Pd/C / acetic acid / 0.5 h / 760 Torr / Ambient temperature 2: 90 percent / sodium azide / dimethylsulfoxide / 3 h / 80 °C 3: 96 percent / Bu4NBr, KOH / tetrahydrofuran / 1.5 h / Ambient temperature 4: 93 percent / H2 / 10percent Pd/C / ethanol / 1.5 h / 2280 Torr / Ambient temperature 6: 89 percent / aq. NaOH / methanol / 2 h / Ambient temperature 7: 25 percent / sodium cyanoborohydride / acetic acid; methanol / Ambient temperature View Scheme

1: 90 percent / sodium azide / dimethylsulfoxide / 3 h / 80 °C 2: 96 percent / Bu4NBr, KOH / tetrahydrofuran / 1.5 h / Ambient temperature 3: 93 percent / H2 / 10percent Pd/C / ethanol / 1.5 h / 2280 Torr / Ambient temperature 5: 89 percent / aq. NaOH / methanol / 2 h / Ambient temperature 6: 25 percent / sodium cyanoborohydride / acetic acid; methanol / Ambient temperature View Scheme

1: 96 percent / Bu4NBr, KOH / tetrahydrofuran / 1.5 h / Ambient temperature 2: 93 percent / H2 / 10percent Pd/C / ethanol / 1.5 h / 2280 Torr / Ambient temperature 4: 89 percent / aq. NaOH / methanol / 2 h / Ambient temperature 5: 25 percent / sodium cyanoborohydride / acetic acid; methanol / Ambient temperature View Scheme

1: 93 percent / H2 / 10percent Pd/C / ethanol / 1.5 h / 2280 Torr / Ambient temperature 3: 89 percent / aq. NaOH / methanol / 2 h / Ambient temperature 4: 25 percent / sodium cyanoborohydride / acetic acid; methanol / Ambient temperature View Scheme

4-methyl-morpholine; hydrogenchloride T=80°C; 9 h;

sodium cyanoborohydride in methanol; acetic acid Ambient temperature;

2: 89 percent / aq. NaOH / methanol / 2 h / Ambient temperature 3: 25 percent / sodium cyanoborohydride / acetic acid; methanol / Ambient temperature View Scheme

1: 89 percent / aq. NaOH / methanol / 2 h / Ambient temperature 2: 25 percent / sodium cyanoborohydride / acetic acid; methanol / Ambient temperature View Scheme