Multi-step reaction with 12 steps
1.1: hydrogen / palladium 10% on activated carbon / ethanol / 24 h / 20 °C
2.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C
3.1: dichloromethane / 20 °C
4.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
5.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C
6.1: 2-(diethylamino)ethanethiol hydrochloride; sodium t-butanolate / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere; Reflux
6.2: 0 °C / pH 3 - 4
7.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 0.5 h / 0 °C
8.1: sodium acetate / (diphenylphosphin)ferrocene; palladium diacetate / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere
9.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; ethanol / 16 h / 20 °C
10.1: lithium hydroxide / tetrahydrofuran; methanol / 48 h / 75 °C
10.2: 20 °C / pH 5 - 6
11.1: HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C
11.2: 0.5 h / 20 °C
12.1: Daicel CHIRALPAK IA / ethanol; hexane; diethylamine / Resolution of racemate
With
2-(diethylamino)ethanethiol hydrochloride; hydrogen; sodium acetate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; lithium hydroxide; sodium t-butanolate;
dmap; (diphenylphosphin)ferrocene; palladium 10% on activated carbon; palladium diacetate;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; diethylamine; N,N-dimethyl-formamide;