1.1: 89 percent / trimethylamine hydrochloride / CH2Cl2 / 4 h / cooling 2.1: 80 percent / NaH / dimethylformamide / 4 h / Heating 3.1: 75 percent / potassium carbonate / 1,2-dichloro-ethane / 4 h / Heating 4.1: hydrogen chloride / 1,2-dichloro-ethane / 0.75 h 4.2: 96 percent / ethanol / 1.5 h / Heating View Scheme

1.1: 80 percent / NaH / dimethylformamide / 4 h / Heating 2.1: 75 percent / potassium carbonate / 1,2-dichloro-ethane / 4 h / Heating 3.1: hydrogen chloride / 1,2-dichloro-ethane / 0.75 h 3.2: 96 percent / ethanol / 1.5 h / Heating View Scheme

1: borane-THF / tetrahydrofuran 2: triethylamine / toluene 3: sodium hydride / N,N-dimethyl-formamide 4: 10 palladium on activated charcoal; hydrogen; acetic acid / isopropyl alcohol View Scheme

1.1: sodium methylate 2.1: lithium aluminium tetrahydride / tetrahydrofuran 3.1: (2S,3S)-(+)-di-O-(p-toluoyl)-tartaric acid 4.1: toluene / 3.75 h / 100 - 105 °C / Large scale reaction 4.2: 1 h / 60 °C 4.3: 25 - 35 °C 5.1: water; sodium hydroxide / isopropyl alcohol / 82 - 85 °C / Large scale reaction View Scheme

1.1: di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium; (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; Jorgensen's catalyst; trichloroacetic acid / 1,2-dichloro-ethane / 20 °C / |Inert atmosphere 2.1: sodium tetrahydroborate / dichloromethane; ethanol / 0.33 h / -78 °C / |Inert atmosphere 3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 10 h / 85 °C / |Inert atmosphere 4.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 4.2: 1 h / 20 °C / |Inert atmosphere 5.1: hydrazine hydrate / ethanol / 0.58 h / 20 - 85 °C / |Inert atmosphere 6.1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 2.5 h / 20 °C / |Inert atmosphere View Scheme

1: sodium hydride / N,N-dimethyl-formamide 2: 10 palladium on activated charcoal; hydrogen; acetic acid / isopropyl alcohol View Scheme

hydrogenchloride in isopropyl alcohol T=30 - 35°C; pH=3 - 4; 2 h; Purification / work up;

sodium hydroxide in water