1.1: carbon tetrabromide / 10 h / 60 °C 2.1: triethylamine; lithium hexamethyldisilazane / toluene / 2.83 h / -60 °C / Inert atmosphere 2.2: 0.17 h 2.3: Cooling with ice 3.1: hydrogen / 5 palladium on charcoal / methanol / 18 h / 20 °C / 3000.3 Torr 4.1: thionyl chloride / toluene / 4 h / 90 °C 5.1: triethylamine / dichloromethane / 0.83 h / 20 °C / Cooling with ice 6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / Inert atmosphere; Reflux 6.2: 0.5 h / 20 °C / Cooling with ice View Scheme

1.1: anhydrous xylene / 16 h / 120 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 16.67 h / 0 - 48 °C 3.1: water; acetone / 46 - 58 °C / |Resolution of racemate 4.1: sodium hydroxide; water / dichloromethane 4.2: 22 h / 24 °C / 3750.38 Torr 5.1: dl-methionine; methanesulfonic acid / 16 h / 80 °C View Scheme