Multi-step reaction with 13 steps
1: 100 percent / H2 / PtO2 / acetic acid / 18 h / 2327.2 Torr
2: 90 percent / 18 h / Ambient temperature
3: thionyl chloride / benzene / 1 h / Heating
4: diethyl ether / 1 h / 25 °C
5: HBr / diethyl ether
6: 91 percent / sodium azide / methanol; H2O / 3.5 h / Ambient temperature
7: p-toluenesulfonic acid / benzene / 6 h / Heating
8: H2 / 10percent Pd/C / 18 h / 517.1 Torr
9: 2.) N-methylmorpholine / 1.) methanol, reflux, 1 h, 2.) methanol, reflux, 3 h
10: 94 percent / trifluoroacetic acid, 0.1 N HCl / 55 - 60 °C
11: 70 percent / sodium ditionite / dimethylformamide; H2O / 0.33 h / 55 °C
12: pyridine, concd. HCl / methanol / 1 h / Heating
13: air / methanol / 4 h
With
4-methyl-morpholine; pyridine; hydrogenchloride; thionyl chloride; sodium azide; sodium dithionite; air; hydrogen bromide; hydrogen; toluene-4-sulfonic acid; trifluoroacetic acid;
platinum(IV) oxide; palladium on activated charcoal;
In
methanol; diethyl ether; water; acetic acid; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm00356a004