Multi-step reaction with 10 steps
1.1: sodium methylate; hydroxylamine hydrochloride / ethanol / 20 °C / Inert atmosphere
2.1: acetic acid; zinc / 3 h / 20 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 4.66 h / 70 °C / Inert atmosphere; Cooling with ice
3.2: 3 h / 115 °C / Inert atmosphere
4.1: boron tribromide / dichloromethane / -78 - 20 °C / Inert atmosphere
5.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 72 h / 0 - 20 °C / Inert atmosphere
6.1: methylhydrazine / ethanol / 1.5 h / 80 °C / Inert atmosphere
7.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 72 h / 85 °C / Inert atmosphere
8.1: hydrogenchloride / 1,4-dioxane; methanol / 1 h / 0 - 20 °C / Inert atmosphere
9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane; tetrahydrofuran / 20 - 50 °C / Inert atmosphere
10.1: hydrogenchloride / tetrahydrofuran; 1,4-dioxane; methanol / 0 - 20 °C / Inert atmosphere
With
hydrogenchloride; dmap; hydroxylamine hydrochloride; sodium methylate; boron tribromide; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; methylhydrazine; zinc; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; acetonitrile;
5.1: |Mitsunobu Displacement;
DOI:10.1021/jm301499r