hydrogenchloride 15 h; Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts;

sodium tetrahydroborate

hydrogenchloride 15 h; Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts;

hydrogenchloride

1.1: pyridinium p-toluenesulfonate / ethyl acetate / 0 - 20 °C 2.1: n-butyllithium / tetrahydrofuran / -78 - 0 °C 3.1: 1H-imidazole; iodine; triphenylphosphine / 60 °C 4.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 2 h / -78 °C 5.1: piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / benzene / 20 °C 6.1: pyridinium p-toluenesulfonate / methanol / 0 °C 7.1: copper/silver activated zinc; water / methanol / 16 h / 40 - 45 °C 8.1: lithium hydroxide hydrate / methanol; water / 24 h / 0 °C 8.2: Saturated solution View Scheme

1: tetrahydrofuran / 3 h / Heating 2: H2 / 10 percent Pd/C / ethyl acetate; methanol / 20 °C View Scheme

1.1: HCl / dioxane / 0.42 h / 20 °C 2.1: 15.0 g / imidazole / tetrahydrofuran / 1.5 h / 20 °C 3.1: 4.20 g / aq. CF3COOH / CH2Cl2 / 0.33 h / -15 °C 4.1: 85 percent / pyridinium chloroformate / CH2Cl2 / 16 h / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -100 °C 5.2: tetrahydrofuran; hexane / 3 h / -100 - -78 °C 6.1: 5.20 g / L-Selectride / tetrahydrofuran / -78 - 0 °C 7.1: 3.72 g / diisopropyl azodicarboxylate; Ph3P / tetrahydrofuran / 3 h / 20 °C 8.1: Et4NF / acetonitrile / 1 h / 20 °C 9.1: 0.94 g / CF3COOH / CH2Cl2 / 0.25 h / 20 °C View Scheme