Multi-step reaction with 11 steps
1: 92 percent / piperidine, glacial acetic acid / CHCl3 / 14 h / Heating
2: 90 percent / sodium borohydride / ethanol / 0.67 h / 15 - 20 °C
3: 55 percent / Cu, pyridine / methanol / 36 h / Heating
4: 88 percent / lithium aluminium hydride / diethyl ether / Heating
5: 92 percent / pydidinum chlorochromate, celite, sodium acetate / CH2Cl2 / 5 h
6: 96 percent / diethyl ether; tetrahydrofuran / -60 °C
7: 95 percent / MnO2 / CHCl3 / 72 h / Ambient temperature
8: 97 percent / potassium t-butoxide / diethyl ether / 16 h / 1.) ether, 16 h
9: 87 percent / NaCl, water / dimethylsulfoxide / 10 h / 150 °C
10: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C
11: 99 percent / triethylamine / benzene / 16 h / 60 °C
With
piperidine; pyridine; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; Celite; potassium tert-butylate; water; sodium acetate; copper; acetic acid; triethylamine; pyridinium chlorochromate; sodium chloride;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; benzene;
DOI:10.1016/S0040-4020(01)87743-7