Multi-step reaction with 13 steps
1.1: oxalyl dichloride; dmap / dichloromethane / 20 °C
2.1: triethylamine / dichloromethane / 0 - 20 °C
3.1: tetrahydrofuran / 2 h / 20 °C
4.1: triethylsilane; boron trifluoride diethyl etherate / acetonitrile / 2 h / 0 - 60 °C
5.1: tert-butylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
5.2: 1.5 h / -78 - 60 °C
6.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate; methanol; water; sodium hydroxide / 0.25 h
7.1: water; acetic acid / 7 h / 100 °C
8.1: dmap; triethylamine / acetonitrile / 1 h / 20 °C
9.1: thiourea; trimethylsilyl trifluoromethanesulfonate / 1,4-dioxane / 3 h / 80 °C
9.2: 18 h / 20 °C
10.1: tri tert-butylphosphoniumtetrafluoroborate; N-Methyldicyclohexylamine; tris-(dibenzylideneacetone)dipalladium(0) / 1-methyl-pyrrolidin-2-one / 0.33 h / 160 °C / Microwave irradiation
11.1: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 2068.65 Torr
12.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 90 °C
13.1: triethylamine / acetonitrile / 18 h / 60 °C
With
methanol; triethylsilane; dmap; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; cerium(III) chloride heptahydrate; trimethylsilylazide; N-Methyldicyclohexylamine; palladium 10% on activated carbon; boron trifluoride diethyl etherate; tert-butylmagnesium chloride; water; hydrogen; di(n-butyl)tin oxide; acetic acid; triethylamine; thiourea; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate;
In
tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; toluene; acetonitrile;