1: 1.) hydroxybenzotriazole (HOBt), EDCI, 2.) N-methylmorpholine (NMM) / 1.) DMF, 40 min, 2.) DMF, a) 0 deg C, 2 h, b) RT, overnight 2: 4 N HCl / dioxane / 1 h / Ambient temperature 3: 1.) hydroxybenzotriazole (HOBt), EDCI, 2.) N-methylmorpholine (NMM) / 1.) DMF, 40 min, 2.) DMF, a) 0 deg C, 2 h, b) RT, overnight 4: 4 N HCl / dioxane / 1 h / Ambient temperature 5: 1.) hydroxybenzotriazole (HOBt), EDCI, 2.) N-methylmorpholine (NMM) / 1.) DMF, 40 min, 2.) DMF, a) 0 deg C, 2 h, b) RT, overnight 6: 4 N HCl / dioxane / 1 h / Ambient temperature 7: triethylamine, DCM / dimethylformamide / 2 h / 0 - 20 °C 8: NaI, NaHCO3 / dimethylformamide / 18 h / Ambient temperature 9: NaBH4 / methanol 10: 99 percent / H2 / 10percent Pd(OH)2/C / aq. acetic acid / 4 h View Scheme

sodium hydrogencarbonate in water; toluene

sodium hydrogencarbonate in water; toluene T=20°C; Schotten Baumann acylation; 1 h;