in methanol T=120°C; 0.666667 h; microwave irradiation;

palladium 10 on activated carbon; hydrogen in methanol T=20°C; 6 h; regioselective reaction;

1: ethanol / 6 h / 20 °C / |Inert atmosphere 2: sodium azide; copper diacetate / methanol / 18 h / 55 °C 3: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 20 °C View Scheme

1: sodium azide; copper diacetate / methanol / 18 h / 55 °C 2: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 20 °C View Scheme

1: manganese(IV) oxide / acetone / 2 h / 20 °C / |Inert atmosphere 2: ethanol / 6 h / 20 °C / |Inert atmosphere 3: sodium azide; copper diacetate / methanol / 18 h / 55 °C 4: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 20 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / |Inert atmosphere 1.2: 1 h / -78 - -20 °C / |Inert atmosphere 1.3: 1 h / -20 - 20 °C / |Inert atmosphere 2.1: manganese(IV) oxide / acetone / 2 h / 20 °C / |Inert atmosphere 3.1: ethanol / 6 h / 20 °C / |Inert atmosphere 4.1: sodium azide; copper diacetate / methanol / 18 h / 55 °C 5.1: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 20 °C View Scheme

1.1: sodium hydride / dimethyl sulfoxide / 0.33 h / 20 °C / Cooling with ice 1.2: 2 h / 20 °C 2.1: methanol / 1.5 h / 110 °C / microwave irradiation View Scheme

trifluoroacetic acid 48 h; Reflux;

hydrogenchloride 3 h; Heating;

1: 1) POCl3; 2) NH2OH 2: 29 percent / ethanol / 5 h / Heating View Scheme