Multi-step reaction with 13 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C
1.2: 1.5 h / 20 °C / cooling with ice
2.1: iodine / ethyl acetate; acetonitrile / 16.75 h / 0 - 20 °C / Inert atmosphere; Darkness
3.1: silver tetrafluoroborate / N,N-dimethyl-formamide; tert-butyl alcohol / 16 h / 80 °C
4.1: Chiralpak AD / n-heptane; ethanol
5.1: lithium hydroxide monohydrate / ethanol; water / 100 °C
6.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 0.5 h / 20 °C
7.1: dmap; triethylamine / dichloromethane / 16 h / 20 °C
8.1: sodium hydrogencarbonate / chloroform / 16 h / 0 - 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 - 20 °C
10.1: trifluoroacetic acid; trifluorormethanesulfonic acid / methoxybenzene / 24 h / 20 - 73 °C
11.1: sodium t-butanolate / tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tert-butyl XPhos / toluene / 16 h / 105 °C / Inert atmosphere; Sealed vial
12.1: hydrogenchloride / 1,4-dioxane; water / 16 h / 20 °C
13.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 0 - 20 °C
With
hydrogenchloride; dmap; silver tetrafluoroborate; lithium hydroxide monohydrate; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium t-butanolate;
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tert-butyl XPhos;
In
tetrahydrofuran; 1,4-dioxane; ethanol; n-heptane; dichloromethane; chloroform; water; ethyl acetate; methoxybenzene; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;