Multi-step reaction with 15 steps
1.1: N,N-dimethyl-formamide / 20 h / 60 °C
2.1: Iodine monochloride; acetic acid / N,N-dimethyl-formamide / 3.67 h / 60 °C
3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
4.1: diisobutylaluminium hydride / toluene / 3 h / 0 °C
5.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 0 - 20 °C
6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
7.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 0.17 h / Inert atmosphere
7.2: 8 h / 65 °C
8.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C
9.1: caesium carbonate / tetrahydrofuran; methanol / 4 h / 20 °C
10.1: tetra-(n-butyl)ammonium iodide; sodium hydroxide / dichloromethane; water; toluene / 20 h / 20 °C
11.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
11.2: 0.75 h / 20 °C
12.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr
13.1: N-ethyl-N,N-diisopropylamine / dichloromethane; isopropyl alcohol / 15 h / 60 °C
14.1: pyridine / dichloromethane / 10 h / 20 °C
15.1: lanthanum(III) chloride bis(lithium chloride) complex / tetrahydrofuran / 0.33 h / 20 °C
15.2: 0.5 h / 0 °C / Supercritical conditions; Resolution of racemate
With
pyridine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; palladium 10% on activated carbon; lanthanum(III) chloride bis(lithium chloride) complex; hydrogen; Iodine monochloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene;