N,N,N',N',N'',N''-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine 1.) THF, hexane, -5 deg C, 30 min, 2.) THF, RT, 2 h; Yield given. Multistep reaction;

1.1: 4-(N,N-dimethlyamino)pyridine / anhydrous dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 6.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 6.2: 1 h / 0 - 5 °C View Scheme

Porcine Pancreas Lipase T=50 - 60°C; 21 h;

hydrogen; ruthenium(IV) oxide; methyl iodide T=220°C; P=205200 Torr; Yield given. Yields of byproduct given;

1: LDA 2: 60 percent / F2 / acetonitrile; H2O; CHCl3 / 0 - 20 °C View Scheme

1: With lithium diisopropyl amide in tetrahydrofuran T=20°C; 5 h; 2: With iodine in tetrahydrofuran T=-78 - 20°C; 1.5 h; optical yield given as percent de;

1.1: 4-(N,N-dimethlyamino)pyridine / anhydrous dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: dihydrogen peroxide; lithium hydroxide hydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C 6.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 6.2: 12.5 h / 0 - 5 °C 7.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 7.2: 0.5 h / 0 - 5 °C 8.1: hydrogenchloride / anhydrous dichloroethane; water / 0 - 5 °C / pH 2.5 8.2: 14.25 h / 0 - 30 °C 9.1: N-bromosuccinmide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 10.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 11.1: triethylamine; 2-hydroxy-pyridine / 16 h / 85 - 90 °C 12.1: hydrogen; ethanolamine / palladium 10 on activated carbon / isopropyl alcohol / 3 h View Scheme

1.1: thionyl chloride; N,N-dimethyl-formamide / 1 h / 20 °C / |Cooling with ice 1.2: 1 h / 20 °C / |Inert atmosphere 2.1: magnesium / tetrahydrofuran / |Reflux 2.2: 16 h / 20 °C View Scheme

Rhizomucor miehei lipase in n-heptane T=40°C; 24 h; Enzymatic reaction;

xylene anschliessend Behandeln mit Wasserstoffperoxid in Aether unter Kuehlung;