1: 76 percent / LiAlH4 / tetrahydrofuran / 0 - 20 °C 2: 0.85 g / pyridinium dichromate / CH2Cl2 / 5 h / 20 °C 3: 1.0 g / tetrahydrofuran / 5 h 4: 78 percent / AlCl3 / CH2Cl2 / 1 h / 20 °C 5: H2 / Pd(OH)2 / methanol / 3 h 6: 0.162 g / methanol / 3 h 7: 84 percent / NaH / tetrahydrofuran / 6 h 8: 85 percent / TFA / CH2Cl2 / 1 h / 20 °C View Scheme