Multi-step reaction with 14 steps
1.1: toluene-4-sulfonic acid / acetone / 24 h / Reflux
2.1: hydrogenchloride / water; methanol / 20 °C
3.1: sodium periodate; sodium hydrogencarbonate / water / 3 h / 0 - 8 °C
3.2: 17 h / 20 °C
4.1: hydrogen / palladium 10% on activated carbon / methanol / 3102.97 Torr
5.1: trifluoroacetic acid / acetonitrile; water / 6 h / Reflux
6.1: lithium hexamethyldisilazane; N2,N2-dimethyl-2-methyl-1,2-propanediamine / tetrahydrofuran / 3 h / -78 °C
6.2: 3 h / -78 °C
7.1: pyridine; trichlorophosphate / 12.5 h / 10 - 20 °C
7.2: 0 °C / pH 5.5
8.1: hydrogen / palladium 10% on activated carbon / methanol / 3102.97 Torr
9.1: n-butyllithium; N2,N2-dimethyl-2-methyl-1,2-propanediamine / tetrahydrofuran; TETRAHYDROPYRANE / 1.33 h / -78 °C
9.2: 1.33 h / -78 °C
9.3: -78 °C / pH 7
10.1: triethylamine / dichloromethane / -10 °C
11.1: tetra(n-butyl)ammonium hydrogensulfate; sodium azide / N,N-dimethyl-formamide / 36 h / 90 °C
12.1: triethylamine; hydrogen / palladium 10% on activated carbon / ethanol; water / 16 h / 3102.97 Torr
13.1: potassium hydroxide / water; tetrahydrofuran; methanol / 10 h / 0 °C
13.2: 10 h / 0 - 20 °C
14.1: triethylamine; 2-hydroxypyridin / 48 h / 90 °C
With
pyridine; 2-hydroxypyridin; hydrogenchloride; sodium periodate; n-butyllithium; sodium azide; N2,N2-dimethyl-2-methyl-1,2-propanediamine; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; potassium hydroxide; lithium hexamethyldisilazane; trichlorophosphate;
palladium 10% on activated carbon;
In
tetrahydrofuran; TETRAHYDROPYRANE; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;