Multi-step reaction with 12 steps
1: N,0-dimethylhydroxylamine; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dmap / dichloromethane / 16 h / 20 °C
2: methylmagnesium chloride / tetrahydrofuran / 0.33 h / 12 - 16 °C / Reflux
3: potassium cyanide / ethanol / 16 h / 120 °C / Autoclave
4: sodium hydroxide / water
5: thionyl chloride
6: lithium aluminium tetrahydride / tetrahydrofuran
7: acetonitrile
8: Reprosil Chiral NR / dichloromethane / Resolution of racemate
9: potassium tert-butylate
10: sodium t-butanolate; tert-butyl XPhos / tris(dibenzylideneacetone)dipalladium(0) chloroform complex / toluene / 18 h / 105 °C / Inert atmosphere; Sealed vial
11: Lawessons reagent / 1,4-dioxane / 18 h / 80 °C / Sealed vial
12: hydrogenchloride / 1,4-dioxane / 20 °C
With
Lawessons reagent; hydrogenchloride; potassium cyanide; lithium aluminium tetrahydride; thionyl chloride; potassium tert-butylate; methylmagnesium chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; sodium t-butanolate; N,0-dimethylhydroxylamine; tert-butyl XPhos;
dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; toluene; acetonitrile;