1: 90 percent / pyridinium p-toluenesulfonate (PPTS) / CH2Cl2 2: diisobutylaluminum hydride (DIBAH) / tetrahydrofuran / -50 °C 3: 4-dimethylaminopyridine (DMAP), pyridine / CH2Cl2 4: 93 percent / H2, pyridine / Pd/C / ethyl acetate 5: 82 percent / 2 N aq. HCl / tetrahydrofuran 6: 33 percent / pyridinium dichromate (PDC), 4A molecular sieves / CH2Cl2 View Scheme

1: 90 percent / pyridinium p-toluenesulfonate (PPTS) / CH2Cl2 2: diisobutylaluminum hydride (DIBAH) / tetrahydrofuran / -50 °C 3: 4-dimethylaminopyridine (DMAP), pyridine / CH2Cl2 4: 93 percent / H2, pyridine / Pd/C / ethyl acetate 5: 82 percent / 2 N aq. HCl / tetrahydrofuran View Scheme