Multi-step reaction with 9 steps
1.1: ozone / methanol / 1 h / -78 °C
1.2: 15 h / 20 °C
2.1: acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 21 h / 20 - 40 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -40 °C / Inert atmosphere
3.2: 0.5 h / -40 - 20 °C
4.1: lithium diisopropyl amide; N,N,N,N,N,N-hexamethylphosphoric triamide / n-heptane; tetrahydrofuran; ethylbenzene / 0.08 h / -78 °C / Inert atmosphere
4.2: 1.5 h
5.1: water; sodium tetrahydroborate / ethanol / 5 h / 20 °C
6.1: hydrogen / 10 wt% Pd(OH)2 on carbon / ethanol / 3 h / 60 °C
7.1: sodium carbonate / tetrahydrofuran / 3 h
8.1: triethanolamine; pyridine-SO3 complex; dimethyl sulfoxide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
9.1: 2-methyl-but-2-ene; sodium hypochlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 2.25 h / 20 °C
9.2: 0.02 h
With
N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hypochlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridine-SO3 complex; triethanolamine; water; hydrogen; sodium tris(acetoxy)borohydride; diisobutylaluminium hydride; sodium carbonate; ozone; acetic acid; dimethyl sulfoxide; lithium diisopropyl amide;
10 wt% Pd(OH)2 on carbon;
In
tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; ethylbenzene; water; N,N-dimethyl-formamide; tert-butyl alcohol;