1.1: 77 percent / NaBH4; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 2.1: NaH / dimethylformamide / 0.08 h / 0 °C 2.2: 83 percent / dimethylformamide / 2 h 3.1: 68 percent / H2 / Pd/C / methanol / 2 h / 2068.59 Torr 4.1: NaH / dimethylformamide / 0.08 h / 20 °C 4.2: 87 percent / dimethylformamide / 0.5 h 5.1: CH2Cl2 / 2 h / 20 °C 6.1: 0.505 g / NH3 / CH2Cl2 / 0.17 h / 20 °C View Scheme

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