Multi-step reaction with 11 steps
1.1: borane-THF / tetrahydrofuran / 13 h / 0 - 20 °C
1.2: 22 h / 20 °C
2.1: potassium dihydrogenphosphate; trifluoroacetyl peroxide / dichloromethane / 1 h / 0 °C
2.2: 0.17 h / 20 °C
3.1: dmap; 1H-imidazole / dichloromethane / 20 °C
4.1: n-butyllithium / hexane; tetrahydrofuran / 0.53 h / -78 °C
4.2: 0.5 h / -78 °C
5.1: water; sodium tetrahydroborate / ethanol / 0.13 h / 0 °C
6.1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 0.3 h / 20 °C
7.1: (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide; cesiumhydroxide monohydrate / dichloromethane / 36 h / -60 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.45 h / 0 °C
9.1: hydrogenchloride / water; tetrahydrofuran / 0.67 h / Inert atmosphere
10.1: sodium hydrogencarbonate / 1,4-dioxane; water / 2.25 h
11.1: bis-[(trifluoroacetoxy)iodo]benzene; pyridine hydrogenfluoride / dichloromethane / 0.33 h / 20 °C
With
1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; potassium dihydrogenphosphate; n-butyllithium; borane-THF; cesiumhydroxide monohydrate; trifluoroacetyl peroxide; tetrabutyl ammonium fluoride; water; iodine; sodium hydrogencarbonate; pyridine hydrogenfluoride; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide;
In
tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; water;