sodium tetrahydroborate; trifluoroacetic acid in dichloromethane T=20°C; 0.5 h;

1: 62 percent / lithium aluminum hydride / tetrahydrofuran / 12 h / Heating 2: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: 94 percent / K2CO3 / acetone / 72 h / Heating 2.1: NaH / dimethylformamide / 0.08 h / 0 °C 2.2: 80 percent / dimethylformamide / 0.5 h / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 3.2: 89 percent / hexane; tetrahydrofuran / 12.5 h / -78 - 20 °C 4.1: 62 percent / lithium aluminum hydride / tetrahydrofuran / 12 h / Heating 5.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: NaH / dimethylformamide / 0.08 h / 0 °C 1.2: 80 percent / dimethylformamide / 0.5 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.2: 89 percent / hexane; tetrahydrofuran / 12.5 h / -78 - 20 °C 3.1: 62 percent / lithium aluminum hydride / tetrahydrofuran / 12 h / Heating 4.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: 94 percent / K2CO3 / acetone / 72 h / Heating 2.1: NaH / dimethylformamide / 0.08 h / 0 °C 2.2: 80 percent / dimethylformamide / 0.5 h / 20 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 3.2: 89 percent / hexane; tetrahydrofuran / 12.5 h / -78 - 20 °C 4.1: 62 percent / lithium aluminum hydride / tetrahydrofuran / 12 h / Heating 5.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 1.2: 89 percent / hexane; tetrahydrofuran / 12.5 h / -78 - 20 °C 2.1: 62 percent / lithium aluminum hydride / tetrahydrofuran / 12 h / Heating 3.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C View Scheme

1.1: NaH / dimethylformamide / 0.08 h / 0 °C 1.2: 83 percent / dimethylformamide / 2 h 2.1: 68 percent / H2 / Pd/C / methanol / 2 h / 2068.59 Torr 3.1: NaH / dimethylformamide / 0.08 h / 20 °C 3.2: 87 percent / dimethylformamide / 0.5 h 4.1: CH2Cl2 / 2 h / 20 °C 5.1: 0.505 g / NH3 / CH2Cl2 / 0.17 h / 20 °C View Scheme