Multi-step reaction with 13 steps
1: 93 percent / piperidine / pyridine / 1.) 90 deg C, 6 h; 2.) 130 deg C, 3 h
2: 98 percent / hydrogen / 10 percent Pd on charcoal / ethanol / 2 h / 2585.7 Torr
3: 98 percent / 10 percent sodium hydroxide / ethanol / 100 °C
4: 95 percent / triethylamine / dimethylformamide / 48 h / 20 °C
5: 78 percent / 5 percent sulfuric acid / methanol / 18 h / 20 °C
6: 1.) phosphorous oxychloride / 1.) 20 deg C, 1 h; 2.) 1,2-dichloroethane, 85 deg C, 4 h
7: 86 percent / sodium borohydride / methanol; CH2Cl2 / 0.33 h / 20 °C
8: 70 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 40 °C
9: 92 percent / hydrogen / 10 percent Pd on charcoal / ethanol / 4 h / 2585.7 Torr
10: 73 percent / triethylamine / methanol / 0.1 h / 185 °C / 0.1 Torr
11: 60 percent / 33 percent hydrobromic acid / methanol; acetic acid / 1 h / 20 °C / in the dark
12: 1.) trifluoroacetic acid; 2.) 33 percent hydrobromic acid / 1.) 20 deg C, 10 min; 2.) methanol, acetic acid, 20 deg C, 2.5 h
With
piperidine; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; hydrogen bromide; hydrogen; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; trichlorophosphate;
palladium on activated charcoal;
In
pyridine; methanol; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89134-1