Multi-step reaction with 11 steps
1.1: tetra-(n-butyl)ammonium iodide; sodium hydroxide / water / 72 h / Inert atmosphere
2.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h
3.1: 2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; lithium chloride / dichloromethane / 25 h / Inert atmosphere
4.1: disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 120 h / 23 °C / Inert atmosphere
5.1: trimethylsilyl trifluoromethanesulfonate / benzene / 144 h / 0 - 23 °C / Inert atmosphere
6.1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C / Inert atmosphere
6.2: 3 h / -78 - 0 °C / Inert atmosphere
6.3: 64 h / 0 - 23 °C / Inert atmosphere
7.1: triethylamine / 36 h / 50 °C / Inert atmosphere
8.1: Burgess Reagent / benzene / 8.5 h / Inert atmosphere; Reflux
8.2: 12 h / Inert atmosphere
9.1: cerium(III) chloride; lithium chloride / tetrahydrofuran / 1.5 h / 23 °C / Inert atmosphere
9.2: 0.5 h / -78 °C / Inert atmosphere
10.1: L-Selectride / tetrahydrofuran / 1.5 h / -78 - 0 °C / Inert atmosphere
11.1: thionyl chloride / dichloromethane / 40 h / 23 °C / Inert atmosphere
With
disodium hydrogenphosphate; thionyl chloride; cerium(III) chloride; Burgess Reagent; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; 2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; hydrogen; tetra-(n-butyl)ammonium iodide; L-Selectride; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; sodium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; dichloromethane; water; benzene;
DOI:10.1021/ja303414a