hydrogen; palladium on activated charcoal in ethanol P=1551.44 Torr; 2 h;

1.1: NaBH4 / tetrahydrofuran / 0.5 h 2.1: 10.6 g / imidazole / CH2Cl2 / 0.5 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 97 percent / tetrahydrofuran; hexane / 1 h / -78 °C 4.1: acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 12 h 5.1: 4 percent / CBr4; triphenylphosphine / tetrahydrofuran / 1 h 6.1: sodium azide / dimethylformamide / 0.5 h / 50 °C 7.1: H2 / 10 percent Pd/C / ethanol / 2 h / 1551.44 Torr View Scheme

1.1: 10.6 g / imidazole / CH2Cl2 / 0.5 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 97 percent / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 12 h 4.1: 4 percent / CBr4; triphenylphosphine / tetrahydrofuran / 1 h 5.1: sodium azide / dimethylformamide / 0.5 h / 50 °C 6.1: H2 / 10 percent Pd/C / ethanol / 2 h / 1551.44 Torr View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 97 percent / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 12 h 3.1: 4 percent / CBr4; triphenylphosphine / tetrahydrofuran / 1 h 4.1: sodium azide / dimethylformamide / 0.5 h / 50 °C 5.1: H2 / 10 percent Pd/C / ethanol / 2 h / 1551.44 Torr View Scheme

1: sodium azide / dimethylformamide / 0.5 h / 50 °C 2: H2 / 10 percent Pd/C / ethanol / 2 h / 1551.44 Torr View Scheme

1: 4 percent / CBr4; triphenylphosphine / tetrahydrofuran / 1 h 2: sodium azide / dimethylformamide / 0.5 h / 50 °C 3: H2 / 10 percent Pd/C / ethanol / 2 h / 1551.44 Torr View Scheme

1: acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 12 h 2: 4 percent / CBr4; triphenylphosphine / tetrahydrofuran / 1 h 3: sodium azide / dimethylformamide / 0.5 h / 50 °C 4: H2 / 10 percent Pd/C / ethanol / 2 h / 1551.44 Torr View Scheme