1: With diisobutylaluminium hydride in dichloromethane T=0°C; 2: With hydrogen; palladium on activated charcoal in ethyl acetate Further stages.;

diisobutylaluminium hydride in hexane; toluene T=25°C; 2 h;

hydrogen; palladium on activated charcoal in ethyl acetate 4 h;

1: 96 percent / DIBAL-H / toluene / 1.5 h / -78 °C 2: 91 percent / DBU; LiCl / acetonitrile / 19 h / 25 °C 3: 2.71 g / H2 / Pd/C / ethyl acetate / 20 h / 25 °C / 760 Torr 4: 93 percent / DIBAL-H / hexane; toluene / 2 h / 25 °C View Scheme

1: 99 percent / imidazole / CH2Cl2 / 76 h / 25 °C 2: 96 percent / DIBAL-H / toluene / 1.5 h / -78 °C 3: 91 percent / DBU; LiCl / acetonitrile / 19 h / 25 °C 4: 2.71 g / H2 / Pd/C / ethyl acetate / 20 h / 25 °C / 760 Torr 5: 93 percent / DIBAL-H / hexane; toluene / 2 h / 25 °C View Scheme

palladium 10 on activated carbon; hydrogen in ethyl acetate 2 h;

1.1: diisobutylaluminium hydride 2.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / |Inert atmosphere 2.2: -78 - 20 °C / |Inert atmosphere 3.1: tetrahydrofuran / 20 °C / |Inert atmosphere 4.1: NaBO3*4H2O / tetrahydrofuran; water / 2 h / 20 °C / |Inert atmosphere View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine; pyridine 3.1: diisobutylaluminium hydride 4.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / |Inert atmosphere 4.2: -78 - 20 °C / |Inert atmosphere 5.1: tetrahydrofuran / 20 °C / |Inert atmosphere 6.1: NaBO3*4H2O / tetrahydrofuran; water / 2 h / 20 °C / |Inert atmosphere View Scheme

2.1: diisobutylaluminium hydride 3.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / |Inert atmosphere 3.2: -78 - 20 °C / |Inert atmosphere 4.1: tetrahydrofuran / 20 °C / |Inert atmosphere 5.1: NaBO3*4H2O / tetrahydrofuran; water / 2 h / 20 °C / |Inert atmosphere View Scheme