Multi-step reaction with 9 steps
1.1: copper(I) bromide / diethyl ether / 0.5 h / -20 °C / Inert atmosphere
1.2: 16.25 h / -20 °C / Inert atmosphere
1.3: 0 °C
2.1: potassium hydroxide / ethanol; water / 3 h / Reflux
3.1: sodium; isopropyl alcohol / toluene / 8 h / Reflux; Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 0 - 20 °C
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 18 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C / Inert atmosphere
6.2: 2 h / -78 °C / Inert atmosphere
7.1: 20 wt.% Pd(OH)2/C; hydrogen / ethyl acetate / 18 h / 3800.26 Torr
8.1: sodium cyanoborohydride / methanol / 18 h / 20 °C / Inert atmosphere
9.1: potassium carbonate / 7 h / 100 °C
With
n-butyllithium; 20 wt.% Pd(OH)2/C; hydrogen; sodium; sodium cyanoborohydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; isopropyl alcohol; potassium hydroxide; copper(I) bromide;
In
tetrahydrofuran; methanol; hexanes; diethyl ether; ethanol; water; ethyl acetate; toluene;
DOI:10.1016/j.tet.2011.05.102