1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 °C / |Inert atmosphere 1.2: 1.75 h / 0 - 20 °C 2.1: triethylamine / dichloromethane / 0 °C / |Inert atmosphere 3.1: hydrogen; potassium hydroxide; 5 palladium on charcoal / methanol / 5 h 4.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 °C / |Inert atmosphere; |Reflux 5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 - 20 °C 5.2: 0.5 h 6.1: acetic acid / tetrahydrofuran; water / 20 °C 7.1: hydrogen; 5 palladium on charcoal / methanol / 5 h / 20 °C 8.1: sodium hydroxide / methanol / 1 h / 20 °C 9.1: potassium carbonate; tetrabutylammomium bromide / acetone / 30 °C 10.1: water; potassium hydroxide / methanol / 3 h / |Reflux 10.2: pH 2 View Scheme