Multi-step reaction with 9 steps
1.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 18 h / 23 - 90 °C
2.1: acetic acid; tin(ll) chloride / 1,2-dimethoxyethane; ethanol / 17 h / 23 - 60 °C
3.1: sulfuric acid / 1,2-dimethoxyethane; water / 23 °C
3.2: 0 °C
4.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 24 h / 23 - 90 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 4.5 h / 0 °C
6.1: dmap; triethylamine / dichloromethane / 1 h / 23 °C
7.1: hydrogen / palladium on activated charcoal / ethyl acetate / 96 h / 23 °C
8.1: pyridinium p-toluenesulfonate / methanol / 4.5 h
9.1: Chiracel-OD / hexane; isopropyl alcohol / Resolution of racemate
With
dmap; lithium aluminium tetrahydride; sulfuric acid; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; acetic acid; triethylamine; tin(ll) chloride;
tetrakis(triphenylphosphine) palladium(0); palladium on activated charcoal;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;