1: samarium diiodide / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C / Inert atmosphere 2: hydrogenchloride / methanol / 4 h / 20 °C 3: palladium 10 on activated carbon; formic acid / methanol / 12 h / Inert atmosphere View Scheme

1.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 1.2: 6 h / -78 - 20 °C / Inert atmosphere 2.1: palladium 10 on activated carbon; hydrogen / methanol / 1 h / 20 °C 3.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C / Inert atmosphere 3.2: 4 h / 20 °C / Saturated solution 4.1: samarium diiodide / tetrahydrofuran; tert-butyl alcohol / 5 h / -78 °C / Inert atmosphere 5.1: hydrogenchloride / methanol / 4 h / 20 °C 6.1: palladium 10 on activated carbon; formic acid / methanol / 12 h / Inert atmosphere View Scheme

methanol; sodium hydroxide T=20°C;

1.1: acetonitrile / |Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / |Inert atmosphere 2.2: -78 - 20 °C / |Inert atmosphere 3.1: hydrogenchloride; palladium on carbon; hydrogen / ethyl acetate / 48 h / 20 °C / 760.05 Torr / |Inert atmosphere View Scheme

in water T=80°C; 16 h;

methanol; sulfuric acid

potassium hydroxide; trifluoroacetic acid 2.) MeOH; Yield given. Multistep reaction;

1.1: trifluoromethanesulfonyl azide; potassium carbonate; copper(II) sulfate / methanol; H2O; CH2Cl2 / 3 h / 20 °C 2.1: 87 percent / triethylamine; 4-dimethylaminopyridine / CH2Cl2; dimethylformamide / 24 h / 20 °C 3.1: thionyl chloride; triethylamine / CH2Cl2 / 0.5 h / 0 °C 4.1: 1.09 g / sodium periodate; ruthenium(III) chloride trihydrate / CCl4; acetonitrile; H2O / 2 h / 20 °C 5.1: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 2 h / Heating 5.2: 87 percent / sulfuric acid / toluene; tetrahydrofuran; H2O / 1 h / 20 °C 6.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 7.1: 87 percent / sodium borohydride / propan-2-ol / 24 h / Heating View Scheme

Novozym 435 in 1,4-dioxane T=80°C; P=760.051 Torr; Enzymatic reaction;

1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane