1.1: methanesulfonic acid / 16 h / 80 °C / Inert atmosphere; Industry scale 2.1: hydrogen / palladium 10 on activated carbon / methanol / 40 °C / 3102.97 Torr / Industry scale 3.1: potassium carbonate / potassium iodide / isobutyramide / 60 - 90 °C / Industry scale 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 20.5 h / -50 - 20 °C / Industry scale 4.2: 15 °C / Industry scale 5.1: thionyl chloride / acetonitrile / 5 - 18 °C / Industry scale 6.1: potassium hydroxide / toluene; water / 0.33 h / 12.5 °C / Industry scale; Inert atmosphere 6.2: 1.65 h / 12.5 - 14.6 °C / Industry scale; Inert atmosphere 7.1: (9R)-1-[3,5-bis(trifluoromethyl)benzyl]cinchonan-1-ium-9-ol bromide / toluene; water / 16 h / 10 °C / Industry scale; Inert atmosphere 8.1: toluene / 6.67 h / 90 °C / Industry scale 9.1: hydrogen / palladium 10 on activated carbon / toluene; methanol / 20 - 27 °C / 3102.97 Torr / Industry scale 9.2: 20 °C / pH 6.3 / Industry scale View Scheme

1.1: 78 percent / HCl(g) / 72 h / 80 °C 2.1: 75 percent / hydrogen / 10 percent Pd on charcoal / ethanol / 5 h / 20 °C / 1551.44 Torr 3.1: NaNO2; HCl / 0 °C 3.2: 35 percent / CuBr; HBr / Heating View Scheme

water T=165°C; Erwaermen des Reaktionsprodukts mit Eisen und wss.-aethanol. HCl;

1: With methanesulfonic acid T=80°C; 16 h; Inert atmosphereLarge scale; 2: With palladium 10 on activated carbon; hydrogen in methanol T=23 - 40°C; P=3102.97 Torr; Large scale;

1: methanesulfonic acid / 16 h / 80 °C / Inert atmosphere; Industry scale 2: hydrogen / palladium 10 on activated carbon / methanol / 40 °C / 3102.97 Torr / Industry scale View Scheme