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

hydrogen; palladium 10 on activated carbon in dichloromethane P=103.432 Torr; 15 h;

1.1: zinc(II) hydroxide / water; tert-butyl methyl ether / 1 h / Inert atmosphere 1.2: 24 h 2.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C 2.2: 1 h / 20 °C 3.1: potassium tert-butylate / tetrahydrofuran / 0.83 h / 0 - 20 °C 3.2: 3 h 4.1: Dess-Martin periodane / dichloromethane / 2 h 5.1: hydrogen / palladium 10 on activated carbon / dichloromethane / 15 h / 103.43 Torr View Scheme

1.1: 1H-imidazole / dichloromethane / 15 h 1.2: 0 °C / pH 3 - 4 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C 2.2: 15 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C 4.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.75 h / -78 °C 4.2: 0.5 h / -78 °C 5.1: zinc(II) hydroxide / water; tert-butyl methyl ether / 1 h / Inert atmosphere 5.2: 24 h 6.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C 6.2: 1 h / 20 °C 7.1: potassium tert-butylate / tetrahydrofuran / 0.83 h / 0 - 20 °C 7.2: 3 h 8.1: Dess-Martin periodane / dichloromethane / 2 h 9.1: hydrogen / palladium 10 on activated carbon / dichloromethane / 15 h / 103.43 Torr View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C 1.2: 15 h / 0 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C 3.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.75 h / -78 °C 3.2: 0.5 h / -78 °C 4.1: zinc(II) hydroxide / water; tert-butyl methyl ether / 1 h / Inert atmosphere 4.2: 24 h 5.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C 5.2: 1 h / 20 °C 6.1: potassium tert-butylate / tetrahydrofuran / 0.83 h / 0 - 20 °C 6.2: 3 h 7.1: Dess-Martin periodane / dichloromethane / 2 h 8.1: hydrogen / palladium 10 on activated carbon / dichloromethane / 15 h / 103.43 Torr View Scheme

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C 2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.75 h / -78 °C 2.2: 0.5 h / -78 °C 3.1: zinc(II) hydroxide / water; tert-butyl methyl ether / 1 h / Inert atmosphere 3.2: 24 h 4.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C 4.2: 1 h / 20 °C 5.1: potassium tert-butylate / tetrahydrofuran / 0.83 h / 0 - 20 °C 5.2: 3 h 6.1: Dess-Martin periodane / dichloromethane / 2 h 7.1: hydrogen / palladium 10 on activated carbon / dichloromethane / 15 h / 103.43 Torr View Scheme

1.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.75 h / -78 °C 1.2: 0.5 h / -78 °C 2.1: zinc(II) hydroxide / water; tert-butyl methyl ether / 1 h / Inert atmosphere 2.2: 24 h 3.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 °C 3.2: 1 h / 20 °C 4.1: potassium tert-butylate / tetrahydrofuran / 0.83 h / 0 - 20 °C 4.2: 3 h 5.1: Dess-Martin periodane / dichloromethane / 2 h 6.1: hydrogen / palladium 10 on activated carbon / dichloromethane / 15 h / 103.43 Torr View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 0.83 h / 0 - 20 °C 1.2: 3 h 2.1: Dess-Martin periodane / dichloromethane / 2 h 3.1: hydrogen / palladium 10 on activated carbon / dichloromethane / 15 h / 103.43 Torr View Scheme

1: Dess-Martin periodane / dichloromethane / 2 h 2: hydrogen / palladium 10 on activated carbon / dichloromethane / 15 h / 103.43 Torr View Scheme

1: With tert-butylamine in ethyl acetate T=20°C; 2: With formic acid in water; ethyl acetate pH=5;