1: 93 percent / 66percent aq. AcOH / 1 h / Ambient temperature 2: 1.) 10percent aq. H2SO4, 2.) Ac2O, pyridine / 1.) ethanol, 3.5 h View Scheme

potassium hydroxide; sulfuric acid 1.) ethanol, 120 deg C, 4 h, 2.) ethanol, reflux, 4 h; Yield given. Multistep reaction;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in toluene 12 h; Heating; Yield given. Yields of byproduct given;

1.1: tert-butyl methyl ether / 2.17 h / 15 - 32 °C / Industry scale 1.2: 2 h / Industry scale 2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 - 32 °C / Industry scale 2.2: 0.5 h / 40 - 50 °C / Industry scale 2.3: 40 °C / pH 8 - 9 / Industry scale 3.1: hydrogen; potassium tert-butylate / Pearlman's catalist / tetrahydrofuran / 45 - 55 °C / 3361.55 - 4137.29 Torr / Industry scale 4.1: hydrogenchloride / water; isopropanol acetate / Industry scale 5.1: Chiralpak AZ column / dichloromethane; acetonitrile; methanol / Resolution of racemate; Multicolumn chromatography View Scheme

1: lilolidine; oxalyl dichloride in diethyl ether T=0°C; 0.5 - 0.75 h; 2: sodium methylate in methanol; diethyl ether T=-78 - 20°C;

1: lilolidine; oxalyl dichloride in tetrahydrofuran T=0°C; 2.5 h; 2: methanol; sodium methylate in tetrahydrofuran T=-78°C;

1: lilolidine; oxalyl dichloride in diethyl ether T=0°C; 0.666667 h; 2: sodium methylate in methanol; diethyl ether T=-78 - 24°C; 2 h;

1: lilolidine; oxalyl dichloride in tert-butyl methyl ether T=15 - 32°C; 2.16667 h; Industry scale; 2: methanol in tert-butyl methyl ether 2 h; Industry scale;

1: diethyl ether / -78 °C 2: NaOMe View Scheme

1: diethyl ether / -78 °C 2: NaOMe 3: t-BuOK / tetrahydrofuran 4: aq. HCl View Scheme