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 7.1: tert-butylamine / ethyl acetate / 20 °C 7.2: pH 5 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