1.1: NaBH4; LiCl / 1,2-dimethoxy-ethane; ethanol / 6 h / -15 - -5 °C 1.2: 88 percent / conc. HCl / 1,2-dimethoxy-ethane; ethanol / 0.5 h 2.1: 56 percent / benzoyl peroxide / tetrahydrofuran View Scheme

1: With sodium tetrahydroborate; lithium chloride in ethylene glycol dimethyl ether; ethanol T=-15 - -5°C; 6 h; 2: With hydrogenchloride in ethylene glycol dimethyl ether; ethanol 0.5 h; Further stages.;

1.1: potassium carbonate / acetonitrile / 14 h / 40 °C 2.1: tetrahydrofuran / 0.17 h / 20 °C 3.1: boron trifluoride diethyl etherate / benzene / 2 h / 20 °C / |Inert atmosphere 4.1: sulfuric acid / 24 h / 0 °C / |Reflux 5.1: ethyl mercaptan sodium salt / N,N-dimethyl-formamide / |Reflux 6.1: sodium nitrite; nitric acid / water / 0.5 h 6.2: |Heating 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.75 h / |Inert atmosphere View Scheme

triethylamine in dichloromethane T=20°C; Edman condensation; 6 h;

1: With pyridine; sodium hydroxide T=40°C; pH=9; 1 h; 2: With hydrogenchloride 2 h; Heating;

triethylamine in dichloromethane T=20°C; 1 h;

in acetonitrile Heating;

sulfuric acid in acetone

1: aq. KOH / ethanol / 3 h 2: 8.86 g / aq. H2SO4 / acetone View Scheme

1.1: [bis(triphenyl-λ5-phosphanylidene)ammonium][Cl] / 1,2-dichloro-benzene / 3 h / 180 °C 1.2: -30 - 0 °C / pH 8.5 2.1: hydrogenchloride / acetone / 40 °C View Scheme