1: With palladium on activated charcoal in formic acid T=20°C; 15 h; 2: in formic acid T=35 - 40°C; 24 h;

1: With 1H-imidazole; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl iodide in dichloromethane; isopropanol acetate T=89°C; 19 h; 2: With hydrogenchloride; water in dichloromethane; isopropanol acetate T=50 - 60°C; 3: With sodium hydrogencarbonate in dichloromethane; isopropanol acetate; water

1: (1S)-(2S)-2-(1-ethyl-2-hydroxy-propyl)-4-{4-[4-(4-hydroxy-phenyl)-piperazin-1-yl]-phenyl}-2,4-dihydro-[1,2,4]triazol-3-one hydrochloride With sodium hydroxide in water; dimethyl sulfoxide T=20°C; 0.25 h; 2: (-)-(5R-cis)-5-(2,4-difluorophenyl)-5-[(1H-1,2,4-triazole-1-yl)methyl]-tetrahydro-3-furanmethanol-4-chlorobenzene sulphonate in water; dimethyl sulfoxide T=10 - 40°C; 10 - 12 h; Product distribution / selectivity;

1.1: 93 percent / K2CO3 / dimethylformamide / 110 °C 2.1: 51 percent / BINAP; t-BuONa / Pd2(dba)3 / toluene / 12 h / 80 °C 3.1: HCOOH / Pd/C 3.2: NH4OH / methanol / Heating View Scheme

1.1: 51 percent / BINAP; t-BuONa / Pd2(dba)3 / toluene / 12 h / 80 °C 2.1: HCOOH / Pd/C 2.2: NH4OH / methanol / Heating View Scheme

1.1: 51 percent / BINAP; t-BuONa / Pd2(dba)3 / toluene / 12 h / 80 °C 2.1: HCOOH / Pd/C 2.2: NH4OH / methanol / Heating View Scheme

hydrogenchloride in methanol

1: DMAP 2: Cs2CO3 / dimethylformamide / Heating 3: aq. HCl / methanol View Scheme

1: Cs2CO3 / dimethylformamide / Heating 2: aq. HCl / methanol View Scheme

1.1: magnesium / tert-butyl methyl ether / 4 h / 55 °C 1.2: -10 - 0 °C 1.3: 3 h / 25 - 50 °C 2.1: sodium hydroxide / dimethyl sulfoxide / 5 h / 25 - 30 °C 3.1: water; lithium chloride; sodium tetrahydroborate / isopropyl alcohol / 20 h / -5 - 30 °C 3.2: pH 1 4.1: sodium hydrogencarbonate / toluene / 24 h / -15 °C / Enzymatic reaction 5.1: sodium hydrogencarbonate; iodine / ethyl acetate / 5 h / -15 °C 6.1: dimethyl sulfoxide / 24 h / 25 - 90 °C 6.2: 3 h / 25 - 30 °C 7.1: hydrogenchloride / tert-butyl methyl ether; acetone / 0.5 h / 25 - 30 °C 8.1: triethylamine / dichloromethane / 1 h / 12 - 22 °C 8.2: 4 h / 12 - 25 °C 9.1: 2,6-di-tert-butyl-4-methyl-phenol; sodium hydroxide; water / dimethyl sulfoxide / 0.17 h / 30 °C 9.2: 32 °C 10.1: 1,1'-carbonyldiimidazole / dichloromethane / 2 h / -10 °C / Inert atmosphere 10.2: 22 h / 0 - 30 °C 11.1: N,O-bis-(trimethylsilyl)-acetamide; 1H-imidazole; trimethylsilyl iodide / dichloromethane; isopropanol acetate / 19 h / 89 °C 11.2: 50 - 60 °C View Scheme