hydrogen; acetic acid in methanol

sodium carbonate T=215 - 225°C; anschliessendes Hydrieren an Raney-Nickel bei 150grad/150 at;

1.1: chloro-trimethyl-silane / 96 h / 18 - 25 °C / Inert atmosphere 2.1: diisopropylamine; n-butyllithium / hexane; N,N'-dimethyl-N,N'-propyleneurea; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 25 °C 3.1: diisopropylamine; n-butyllithium / hexane; N,N'-dimethyl-N,N'-propyleneurea; tetrahydrofuran / -78 - 25 °C / Inert atmosphere View Scheme

1.1: chloro-trimethyl-silane / 96 h / 18 - 25 °C / Inert atmosphere 2.1: diisopropylamine; n-butyllithium / hexane; N,N'-dimethyl-N,N'-propyleneurea; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 25 °C 3.1: diisopropylamine; n-butyllithium / hexane; N,N'-dimethyl-N,N'-propyleneurea; tetrahydrofuran / -78 - 25 °C / Inert atmosphere 4.1: water; Ba(OH)2·8H2O / ethanol / Inert atmosphere; Reflux 4.2: 18 - 25 °C / pH 1 - 2 View Scheme

dicyclohexyl-carbodiimide in dichloromethane T=20°C; 4 h;

in dichloromethane T=20°C; 4 h;

in dichloromethane T=20°C; 4 h;

thionyl chloride

sodium azide; sulfuric acid in chloroform T=0 - 50°C; Schmidt reaction; 1 h;

sulfuric acid 24 h; Reflux;