Multi-step reaction with 9 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 - -20 °C / Inert atmosphere
2.1: sulfuric acid; acetic acid / 20 h / 20 °C / Inert atmosphere
3.1: water; sodium hydroxide / ethanol / 1 h / 80 °C / Inert atmosphere
4.1: methanol; dichloromethane; acetonitrile / 10 h / 0 - 5 °C / Inert atmosphere; UV-irradiation
4.2: 1 h / 60 °C / Inert atmosphere
4.3: 48 h / Inert atmosphere
5.1: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere
6.1: ChiralPak AD-H / ethanol / Inert atmosphere; Supercritical conditions; Resolution of racemate
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.82 h / -10 °C / Inert atmosphere
8.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / 1-methyl-pyrrolidin-2-one / 20 h / 98 - 104 °C / Inert atmosphere
9.1: lithium hydroxide / methanol; water / 2 h / 50 °C / Inert atmosphere
9.2: pH 1 - 2 / Inert atmosphere
With
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sulfuric acid; 5%-palladium/activated carbon; water; hydrogen; acetic acid; N-ethyl-N,N-diisopropylamine; sodium hydroxide; lithium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; water; acetonitrile;
1.1: |Baker-Venkataraman Rearrangement;
DOI:10.1021/jm3011542