1: 72 percent / pyridine / 22 °C 2: 93 percent / NaN3 / dimethylformamide / 16 h / 55 °C 3: 51 percent / 1M NaOH / methanol / 22 °C 4: 97 percent / H2 / 10percent Pd/C / H2O; ethanol / 5171.5 Torr View Scheme

lithium hydroxide in ethanol T=20°C; 2 h;

1: 82 percent / triphenyl phosphine; DEAD / tetrahydrofuran; toluene / 20 °C 2: 100 percent / sodium hydroxide / H2O; tetrahydrofuran / 3 h View Scheme

1: 72 percent / pyridine / 22 °C 2: 72 percent / dimethylformamide / 20 h / 55 °C 3: 100 percent / NaOH / H2O; methanol View Scheme

1.1: 1.0M LiOH aq. / ethanol / 2 h / 20 °C 2.1: 2M HCl / dioxane / 19 h / 20 °C 2.2: TEA / ethanol View Scheme

1: 89 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 48 h 2: 1.) Et4NOAc*4H2O, 2.) 1 N NaOH / 1.) benzene, reflux, 1.5 h, 2.) MeOH, 0 deg C 3: 45 percent / LiBH4 / tetrahydrofuran 4: 69 percent / pyridine 5: 34 percent / 1.) Na/NH3 (liq.) / tetrahydrofuran View Scheme

lithium borohydride in tetrahydrofuran T=0 - 20°C; Inert atmosphere;