T=200°C;

2: DMF / Erwaermen des Reaktionsprodukts mit methanol. KOH View Scheme

1: xylene / Erwaermen des Reaktionsprodukts mit KOH in Methanol und Isopropylalkohol 2: 200 °C View Scheme

N,N-dimethyl-formamide Erwaermen des Reaktionsprodukts mit methanol. KOH;

1.1: 100 percent / diethyl ether; tetrahydrofuran / 0.67 h / 20 °C 2.1: 100 percent / conc. hydrochloric acid / 12 h / 20 °C 3.1: 98 percent / lithium aluminum hydride / 1 h / 20 °C 4.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 5.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 5.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 6.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1.1: 100 percent / diethyl ether; tetrahydrofuran / 0.67 h / 20 °C 2.1: 100 percent / conc. hydrochloric acid / 12 h / 20 °C 3.1: 98 percent / lithium aluminum hydride / 1 h / 20 °C 4.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 5.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 5.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 6.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 7.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 8.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 9.1: pyridine / CHCl3 / 3 h / 20 °C 10.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C 11.1: aq. hydrobromic acid / CHCl3; acetic acid / 1.5 h / 20 °C 11.2: 44 percent / tributyltin hydride; α,α'-azobis(isobutyronitrile) / benzene / 1 h / Heating View Scheme

1.1: 100 percent / diethyl ether; tetrahydrofuran / 0.67 h / 20 °C 2.1: 100 percent / conc. hydrochloric acid / 12 h / 20 °C 3.1: 98 percent / lithium aluminum hydride / 1 h / 20 °C 4.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 5.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 5.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 6.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 7.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 8.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 9.1: pyridine / CHCl3 / 3 h / 20 °C 10.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C View Scheme

1: lithium aluminum hydride / tetrahydrofuran / 18 h / 60 °C 2: dichlorodicyanobenzoquinone / dioxane / 15 h / Ambient temperature 3: p-toluenesulfonic acid / CH2Cl2 / 0.5 h / Ambient temperature 4: 72 percent / sodium hydroxide, hydrogen peroxide / methanol; H2O / 1.5 h / Ambient temperature 5: lithium / liquid ammonia; tetrahydrofuran / 1.5 h / -78 °C 6: N,N-diethylcyclohexylamine / dioxane / 1.) 50 deg C, 6 h; 2.) 80 deg C, 2 h 7: aq. HCl; tetrahydrofuran; methanol / Ambient temperature 8: 73 percent / pyridine / 0.5 h / 0 °C 9: 85 percent / dimethylsulfoxide / 4 h / 90 - 100 °C 10: potassium hydroxide / H2O; ethanol / 2 h / Heating 11: methanol; diethyl ether / 1 h / Ambient temperature 12: 81 percent / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) rt, 4.5 h 13: 82 percent / aq. HCl; tetrahydrofuran / 72 h / Ambient temperature 14: 74 percent / pyridine 15: N-bromosuccinimide / CCl4 / 0.33 h / Heating 16: tetra-n-butylammonium fluoride / tetra-n-butylammonium bromide / tetrahydrofuran 17: potassium hydroxide / tetrahydrofuran; methanol View Scheme

1: Cholenic acid With triethylamine; isobutyl chloroformate in tetrahydrofuran T=0°C; 0.166667 h; 2: dimethyl amine in tetrahydrofuran T=0 - 20°C;