1: acetone / 7.42 h / 20 - 60 °C / Resolution of racemate; Industry scale 2: hydrogenchloride / water; tert-butyl methyl ether / 20 - 25 °C View Scheme

1: 4-(N,N-dimethlyamino)pyridine; Fonderma; 2-methylpropane-2-thiol / tetrahydrofuran / 3 h / Reflux 2: pig liver esterase; sodium hydroxide / water / 11 h / 20 °C / pH 7 / aq. phosphate buffer View Scheme

phosphate buffer; porcine pancreatic lipase T=20°C; pH=7.00; 12 h; Enzymatic reaction; Title compound not separated from byproducts;

jones' reagent Yield given. Yields of byproduct given;

lithium hydroxide; ethylaluminum dichloride 1.) CH2Cl2, -78 deg C, 2.) THF, H2O, room temp.; ee.: 93percent; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

sodium hydride in N,N-dimethyl-formamide; mineral oil T=20 - 120°C; 18 h; Product distribution / selectivity;

1: hydrogenchloride / water / 6 h / 20 °C / Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 18 h / 20 - 120 °C 3: sodium hydroxide; water / methanol / 16 h / 20 °C 4: water; acetone / 23 h / 10 - 50 °C 5: hydrogenchloride / water; tert-butyl methyl ether / 1 h / 20 °C / pH 1 View Scheme

1.1: sodium hydrogencarbonate / water 1.2: 20 °C / Darkness 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Reflux 3.1: potassium carbonate / 5 h / 20 °C 4.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 7.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 7.2: 1 h 8.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 9.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 9.2: 0.5 h / -78 °C / Inert atmosphere 9.3: 0.5 h 10.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 11.1: triphenylphosphine / toluene / 3 h / Reflux 12.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 20 °C 13.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 14.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 14.2: 4 °C View Scheme

1: hydrogenchloride / water / 6 h / 20 °C / Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 18 h / 20 - 120 °C View Scheme

1: hydrogenchloride / water / 6 h / 20 °C / Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 18 h / 20 - 120 °C View Scheme