Multi-step reaction with 15 steps
1.1: zinc(II) chloride / N,N-dimethyl-formamide / 3.5 h / 105 °C
2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 0.33 h / 20 °C
2.2: 4 h / 80 °C
3.1: nitric acid / dichloromethane / 1.5 h / 0 - 20 °C
4.1: potassium phosphate / palladium diacetate; tert-butyl XPhos / toluene / 2 h / 100 °C / Inert atmosphere
5.1: boron trichloride / dichloromethane / -78 - -40 °C
6.1: triethylamine / dmap / dichloromethane / 1 h / 0 - 20 °C
7.1: sodium acetate / (diphenylphosphin)ferrocene; palladium diacetate / acetonitrile / 2 h / 100 °C / Inert atmosphere
8.1: hydrogenchloride; water / tetrahydrofuran / 1 h / Reflux
9.1: tin(II) chloride dihdyrate / ethyl acetate / 1 h / 80 °C
9.2: 20 °C / pH 8 - 9
10.1: pyridine / 2 h / 0 - 30 °C
11.1: sodium tetrahydroborate / tetrahydrofuran / 0.5 h / 0 °C
12.1: sodium hydride / dichloromethane; paraoil / 15 h / 0 - 20 °C
13.1: water; lithium hydroxide / tetrahydrofuran; methanol / 12 h / 80 °C
13.2: 20 °C / pH 2 - 3
14.1: HATU / N,N-dimethyl-formamide / 1 h / 20 °C
14.2: 1 h / 20 °C
15.1: Daicel CHIRALPAK AS-H column / methanol; carbon dioxide / Resolution of racemate
With
pyridine; hydrogenchloride; sodium tetrahydroborate; potassium phosphate; tin(II) chloride dihdyrate; water; nitric acid; sodium acetate; boron trichloride; sodium hydride; caesium carbonate; triethylamine; HATU; zinc(II) chloride; lithium hydroxide;
dmap; (diphenylphosphin)ferrocene; palladium diacetate; tert-butyl XPhos;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; carbon dioxide; paraoil; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;