Multi-step reaction with 12 steps
1.1: pyridine / dichloromethane / 3 h / 20 °C
2.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium t-butanolate / toluene / Inert atmosphere
2.2: 6 h / 50 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / hexane; dichloromethane / 1.08 h / -78 - 20 °C / Inert atmosphere
4.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5.1: palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate / tetrahydrofuran / 1.5 h / 20 °C
6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 96 h / 20 °C
7.1: tri-n-butylamine hydrofluoride / tetrahydrofuran / 48 h / 20 °C
8.1: tetra-n-butylammoniumfluoride trihydrate / tetrahydrofuran / 72 h / 20 °C
9.1: N,N-dimethyl-formamide / 1.5 h / -40 °C
9.2: 0.5 h / -40 - 20 °C
10.1: dmap / toluene / 3 h / 20 °C
11.1: tri-n-butylamine hydrofluoride / tetrahydrofuran / 48 h / 20 °C
12.1: Dowex / methanol / 20 h / 50 °C
With
pyridine; dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; palladium 10% on activated carbon; hydrogen; tri-n-butylamine hydrofluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; tetra-n-butylammoniumfluoride trihydrate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium t-butanolate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.3762/bjoc.8.82