1: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) DMF, 15 min, -18 deg C; 2.) 2 h, -10 - -20 deg C; 4 h, room temperature 2: 84 percent / H2 / Pd black / methanol / 12 h 3: 80 percent / HONB, DCCI / dimethylformamide / 1.) 2 h, -20 deg C; 2.) 3 h, room temperature 4: 98 percent / HCl, CH3COOH, C2H5SH / 0.75 h / Ambient temperature 5: 86 percent / N-methylmorpholine / 48 h View Scheme

1: 84 percent / H2 / Pd black / methanol / 12 h 2: 80 percent / HONB, DCCI / dimethylformamide / 1.) 2 h, -20 deg C; 2.) 3 h, room temperature 3: 98 percent / HCl, CH3COOH, C2H5SH / 0.75 h / Ambient temperature 4: 86 percent / N-methylmorpholine / 48 h View Scheme

4-methyl-morpholine 48 h;

1: hydrogenchloride / water / 0.25 h / 25 °C 2: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 3: hydrogenchloride / water / 0.25 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 5: hydrogenchloride / water / 0.25 h / 25 °C 6: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 7: hydrogenchloride / water / 0.25 h / 25 °C 8: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 9: palladium 10 on activated carbon; ammonium formate / methanol / |Reflux View Scheme

1: formamide; sodium methylate / 100 °C 2: hydrogenchloride / water / 0.25 h / 25 °C 3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 4: hydrogenchloride / water / 0.25 h / 25 °C 5: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 6: hydrogenchloride / water / 0.25 h / 25 °C 7: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 8: hydrogenchloride / water / 0.25 h / 25 °C 9: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 10: palladium 10 on activated carbon; ammonium formate / methanol / |Reflux View Scheme

1: hydrogenchloride / water / 0.25 h / 25 °C 2: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 3: hydrogenchloride / water / 0.25 h / 25 °C 4: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 5: hydrogenchloride / water / 0.25 h / 25 °C 6: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 7: palladium 10 on activated carbon; ammonium formate / methanol / |Reflux View Scheme

1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 2: hydrogenchloride / water / 0.25 h / 25 °C 3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 4: hydrogenchloride / water / 0.25 h / 25 °C 5: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 6: palladium 10 on activated carbon; ammonium formate / methanol / |Reflux View Scheme

1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 2: hydrogenchloride / water / 0.25 h / 25 °C 3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 4: palladium 10 on activated carbon; ammonium formate / methanol / |Reflux View Scheme

1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; benzotriazol-1-ol / water / 60 °C / |Microwave irradiation 2: palladium 10 on activated carbon; ammonium formate / methanol / |Reflux View Scheme

palladium 10 on activated carbon; ammonium formate in methanol Reflux;