Multi-step reaction with 13 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 2.83 h / -78 - 20 °C
2.1: acetic acid / ethanol / 7 h / 50 °C
3.1: caesium carbonate / tetrahydrofuran; acetonitrile / 4 h
4.1: pyridine / 18 h
5.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C / Cooling with ice
6.1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane; water / 24 h / 90 °C / Inert atmosphere
7.1: palladium 10% on activated carbon; hydrogen / ethanol / 9 h / Inert atmosphere
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / Cooling with ice
9.1: palladium diacetate; caesium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / tetrahydrofuran / Inert atmosphere; Reflux
10.1: hydroxylamine hydrochloride; sodium acetate / methanol; N,N-dimethyl-formamide
11.1: triethylamine / dichloromethane / Cooling with ice
12.1: trifluorormethanesulfonic acid; methyl-phenyl-thioether / dichloromethane / 40 °C
13.1: methanol; sodium hydroxide / tetrahydrofuran
With
pyridine; methanol; triethylsilane; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; trifluorormethanesulfonic acid; methyl-phenyl-thioether; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; hydrogen; sodium acetate; palladium diacetate; caesium carbonate; acetic acid; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;