1: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C 2: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 3: 30percent NaOMe / methanol / Ambient temperature; pH 11 4: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr View Scheme

1: 83 percent / NaH / tetrahydrofuran / 40 - 70 °C 2: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 3: 30percent NaOMe / methanol / Ambient temperature; pH 11 4: 94 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr View Scheme

1: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C 2: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature 3: 30percent NaOMe / methanol / Ambient temperature; pH 11 4: 84 percent / H2, NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr 5: pyridine / 5 h / Ambient temperature 6: 96 percent / diisopropylammonium-tetrazolide / CH2Cl2 / Ambient temperature View Scheme