triethylsilane; trifluoroacetic acid 5 h; Reflux;

1.1: potassium carbonate / N,N-dimethyl-formamide / 4.5 h / 50 °C 2.1: trifluoroacetic acid; triethylsilane / dichloromethane / 16 h / 0 - 20 °C 3.1: potassium hydroxide; (1S,2R,4S,5R)-1-(anthracen-9-ylmethyl)-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride / toluene; water; ethyl acetate / 4.75 h / -16 °C / |Inert atmosphere 4.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 16 h / 517.16 Torr 5.1: bisphenyl-(pyridin-2-yl)phosphine / tetrahydrofuran / 0.08 h / 0 °C 5.2: 0.5 h 6.1: trifluoroacetic acid; triethylsilane / 5 h / |Reflux View Scheme

1.1: trifluoroacetic acid; triethylsilane / dichloromethane / 16 h / 0 - 20 °C 2.1: potassium hydroxide; (1S,2R,4S,5R)-1-(anthracen-9-ylmethyl)-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride / toluene; water; ethyl acetate / 4.75 h / -16 °C / |Inert atmosphere 3.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 16 h / 517.16 Torr 4.1: bisphenyl-(pyridin-2-yl)phosphine / tetrahydrofuran / 0.08 h / 0 °C 4.2: 0.5 h 5.1: trifluoroacetic acid; triethylsilane / 5 h / |Reflux View Scheme

1.1: potassium hydroxide; (1S,2R,4S,5R)-1-(anthracen-9-ylmethyl)-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride / toluene; water; ethyl acetate / 4.75 h / -16 °C / |Inert atmosphere 2.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 16 h / 517.16 Torr 3.1: bisphenyl-(pyridin-2-yl)phosphine / tetrahydrofuran / 0.08 h / 0 °C 3.2: 0.5 h 4.1: trifluoroacetic acid; triethylsilane / 5 h / |Reflux View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide / 1.5 h / 0 °C 1.2: 18.25 h / 0 - 60 °C 2.1: isopropylmagnesium chloride / tetrahydrofuran / 42.25 h / 0 - 20 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 4.5 h / 50 °C 4.1: trifluoroacetic acid; triethylsilane / dichloromethane / 16 h / 0 - 20 °C 5.1: potassium hydroxide; (1S,2R,4S,5R)-1-(anthracen-9-ylmethyl)-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride / toluene; water; ethyl acetate / 4.75 h / -16 °C / |Inert atmosphere 6.1: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 16 h / 517.16 Torr 7.1: bisphenyl-(pyridin-2-yl)phosphine / tetrahydrofuran / 0.08 h / 0 °C 7.2: 0.5 h 8.1: trifluoroacetic acid; triethylsilane / 5 h / |Reflux View Scheme

CHIRALPAK-IA Resolution of racemate; Purification / work up;