Multi-step reaction with 11 steps
1: triethylamine / dichloromethane / 22 °C
2: ethanol; hexane / Resolution of racemate
3: PS-triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane
4: hydrogen / 10 % Pd(OH)2/C / ethanol / 0.67 h / 22 °C / 760.05 Torr
5: benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine / N,N-dimethyl-formamide / 18 h / 22 °C
6: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 77 h / 20 - 85 °C
7: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water; tert-butyl alcohol / 4 h / 20 °C
8: lithium borohydride / tetrahydrofuran / 0.5 h / 20 °C
9: pyridine; dmap / 0.5 h / 20 °C
10: copper(l) iodide; cesium fluoride / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.42 h / 150 °C / Microwave irradiation
11: methanol; sodium hydroxide; water / tetrahydrofuran / 3 h / 20 °C
With
pyridine; methanol; dmap; sodium hydroxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; lithium borohydride; PS-triphenylphosphine; di-isopropyl azodicarboxylate; water; hydrogen; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; cesium fluoride;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); 10 % Pd(OH)2/C;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;