hydrogen; palladium on activated charcoal in methanol P=760 Torr; Ambient temperature;

lithium hydroxide in tetrahydrofuran; methanol; water T=25°C; 1.2 h;

1: NaH / tetrahydrofuran; dimethylformamide / 10 h / 0 - 25 °C 2: H2 / Pd-C / methanol / 25 °C View Scheme

1: 72 percent / tetrahydrofuran / 2 h / 25 °C 2: 93 percent / imidazole / dimethylformamide / 6 h / 25 °C 3: 87 percent / NaH / dimethylformamide / 48 h / 25 °C 4: 82 percent / AcOH / tetrahydrofuran; H2O / 8 h / 25 °C 5: 95 percent / LiOH / tetrahydrofuran; methanol; H2O / 1.2 h / 25 °C View Scheme

1: 93 percent / imidazole / dimethylformamide / 6 h / 25 °C 2: 87 percent / NaH / dimethylformamide / 48 h / 25 °C 3: 82 percent / AcOH / tetrahydrofuran; H2O / 8 h / 25 °C 4: 95 percent / LiOH / tetrahydrofuran; methanol; H2O / 1.2 h / 25 °C View Scheme

1: 95 percent / HCl (gas) / 2 h / 25 °C 2: 72 percent / tetrahydrofuran / 2 h / 25 °C 3: 93 percent / imidazole / dimethylformamide / 6 h / 25 °C 4: 87 percent / NaH / dimethylformamide / 48 h / 25 °C 5: 82 percent / AcOH / tetrahydrofuran; H2O / 8 h / 25 °C 6: 95 percent / LiOH / tetrahydrofuran; methanol; H2O / 1.2 h / 25 °C View Scheme

1: 87 percent / NaH / dimethylformamide / 48 h / 25 °C 2: 82 percent / AcOH / tetrahydrofuran; H2O / 8 h / 25 °C 3: 95 percent / LiOH / tetrahydrofuran; methanol; H2O / 1.2 h / 25 °C View Scheme

1: 82 percent / AcOH / tetrahydrofuran; H2O / 8 h / 25 °C 2: 95 percent / LiOH / tetrahydrofuran; methanol; H2O / 1.2 h / 25 °C View Scheme