1.1: 1-hydroxybenzotriazole; EDCI / tetrahydrofuran / 0.5 h / 20 °C 1.2: 68 percent / aq. NH3 / tetrahydrofuran / 24 h / 20 °C 2.1: 64 percent / p-TsCl; pyridine / CH2Cl2 / 72 h / 20 °C View Scheme

1.1: oxalyl dichloride / N,N-dimethyl-formamide; toluene / 2.5 h / 20 - 25 °C 2.1: methyl-magnesium chloride / tert-butyl methyl ether; tetrahydrofuran / 0.75 h / 20 °C 2.2: 0.5 h / 3 - 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 60 °C / Reflux View Scheme

1.1: oxalyl dichloride / dichloromethane / 1 h / 20 °C 2.1: ethylmagnesium bromide / dichloromethane; diethyl ether / 0.5 h / Reflux 2.2: 10 h / -25 - -15 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 3.2: 0 - 5 °C View Scheme

ammonium chloride in dichloromethane; water; N,N-dimethyl-formamide; toluene

1: oxalyl chloride; DMF / CH2Cl2 2: CH2Cl2 View Scheme

benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine in DMF (N,N-dimethyl-formamide) T=20°C; 18 h;

EDAC; triethanolamine; benzotriazol-1-ol in N,N-dimethyl-formamide

1.1: oxalyl dichloride / N,N-dimethyl-formamide; toluene / 2.5 h / 20 - 25 °C 2.1: methyl-magnesium chloride / tert-butyl methyl ether; tetrahydrofuran / 0.75 h / 20 °C 2.2: 0.5 h / 3 - 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3.5 h / 60 °C / Reflux 4.1: isopropyl alcohol; water / 4 h / 20 - 35 °C 5.1: potassium hydroxide / toluene; water / 0.25 h / 21 - 25 °C 5.2: 4 h / 100 °C 6.1: triethylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 5 h / 115 °C 7.1: potassium carbonate; water / methanol 8.1: hydrogen bromide / water / pH 1.5 9.1: hydrogen / 5 Pd(II)/C(eggshell) / water / 20 - 50 °C / Autoclave View Scheme

1: 1.) triethylamine, isobutyl chloroformate, 2.) ammonia / 1.) chloroform, 0 deg C, 2 h, 2.) chloroform, RT, overnight 2: 87.3 percent / hydrogen / 10percent palladium on carbon / methanol / 9 h / Ambient temperature 3: 46.1 percent / lithium aluminum hydride / tetrahydrofuran / 33 h / Heating View Scheme