tetrabutylammomium bromide; potassium carbonate in water; toluene 24 h; Ambient temperature;

in acetonitrile T=125°C; P=206859 Torr;

1.1: D-proline / acetonitrile / 3 h / 0 - 20 °C 1.2: NaBH4 / acetonitrile; ethanol / 0.08 h / 0 °C 2.1: 70 percent / Raney-Nickel; AcOH; hydrogen / methanol / 16 h / 20 °C / 3102.97 Torr 3.1: 0.1 g / triethylamine / CH2Cl2 / 1 h / 0 °C 4.1: triethylamine / CH2Cl2 / 1 h / 0 °C 5.1: LiAlH4 / tetrahydrofuran / 4 h / Heating 6.1: 72 percent / anhydrous potassium carbonate / acetonitrile / 12 h / 25 °C View Scheme

1: triethylamine / CH2Cl2 / 0.5 h / 0 °C 2: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 3: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 4: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 5: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 6: 72 percent / anhydrous potassium carbonate / acetonitrile / 12 h / 25 °C View Scheme

1: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: triethylamine / CH2Cl2 / 0.5 h / 0 °C 3: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 4: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 5: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 6: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 7: 72 percent / anhydrous potassium carbonate / acetonitrile / 12 h / 25 °C View Scheme

1: triethylamine / CH2Cl2 / 1 h / 0 °C 2: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 3: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: triethylamine / CH2Cl2 / 0.5 h / 0 °C 5: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 6: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 7: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 8: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 9: 72 percent / anhydrous potassium carbonate / acetonitrile / 12 h / 25 °C View Scheme

1: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 2: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: triethylamine / CH2Cl2 / 0.5 h / 0 °C 4: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 5: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 6: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 7: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 8: 72 percent / anhydrous potassium carbonate / acetonitrile / 12 h / 25 °C View Scheme

1: 88 percent / hydrogen / Pd/C / methanol / 12 h / 760.05 Torr 2: triethylamine / CH2Cl2 / 1 h / 0 °C 3: 0.33 g / sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C 4: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 5: triethylamine / CH2Cl2 / 0.5 h / 0 °C 6: 0.37 g / sodium azide / dimethylformamide / 6 h / 80 °C 7: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 8: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 9: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 10: 72 percent / anhydrous potassium carbonate / acetonitrile / 12 h / 25 °C View Scheme

1: 98 percent / hydrogen / Pd/C / methanol / 2 h / 760.05 Torr 2: 95 percent / triethylamine / CH2Cl2 / 1 h / 0 °C 3: 92 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 4: 72 percent / anhydrous potassium carbonate / acetonitrile / 12 h / 25 °C View Scheme

potassium carbonate in acetonitrile T=20°C; Title compound not separated from byproducts;