Multi-step reaction with 8 steps
1.1: tetrahydrofuran; diethyl ether / 12 h / 0 - 20 °C / Inert atmosphere
2.1: hydrogenchloride / 1,4-dioxane; methanol / 0.5 h / 20 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 - 45 °C / Inert atmosphere
5.1: sodium iodide / N,N-dimethyl-formamide / 6 h / 20 - 90 °C / Inert atmosphere
6.1: methylamine / methanol / 1 h / 20 °C / Inert atmosphere
7.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C
8.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere
8.2: 1 h / 0 - 75 °C / Inert atmosphere
With
hydrogenchloride; sodium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; methylamine; sodium iodide;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; mineral oil;
8.1: Horner-Wadsworth-Emmons olefination / 8.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm300416h