1: dimethyl amine With trimethylaluminum in toluene T=-15 - 0°C; 1 h; 2: (S,E)-ethyl 5-chloro-2-isopropylpent-4-enoate in toluene T=80°C; 22 h; 3: With hydrogenchloride; water in toluene

1: With sodium hydroxide; water in ethanol 18 h; Heating / reflux; 2: With hydrogenchloride in water

1.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 1.2: 12.5 h / 0 - 5 °C 2.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 2.2: 0.5 h / 0 - 5 °C 3.1: hydrogenchloride / anhydrous dichloroethane; water / 0 - 5 °C / pH 2.5 3.2: 14.25 h / 0 - 30 °C 4.1: N-bromosuccinmide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 5.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 6.1: triethylamine; 2-hydroxy-pyridine / 16 h / 85 - 90 °C 7.1: hydrogen; ethanolamine / palladium 10 on activated carbon / isopropyl alcohol / 3 h View Scheme

1.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 1.2: 12.5 h / 0 - 5 °C 2.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 2.2: 0.5 h / 0 - 5 °C 3.1: hydrogenchloride / anhydrous dichloroethane; water / 0 - 5 °C / pH 2.5 3.2: 14.25 h / 0 - 30 °C 4.1: N-bromosuccinmide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 5.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 6.1: triethylamine; 2-hydroxy-pyridine / 16 h / 85 - 90 °C View Scheme