Multi-step reaction with 9 steps
1: 86 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 0.75 h / 25 °C
2: 1.) sodium hydride / 1.) ether, 25 deg C, 45 min, 2.) 3 h
3: 98 percent / hydrogen / 5percent Pd-C / methanol / 12 h / 25 °C
4: 93 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 °C
5: 86 percent / hydrochloric acid / diethyl ether / 3 h / 25 °C
6: 97 percent / pyridine
7: 1.) sodium iodide, 2.) DBU / 1.) DMF, 50 deg C, 3.5 h, 2.) 80 deg C, 3.5 h
8: 1.) sodium hydride, 3.) aluminum chloride, lithium aluminum hydride / 1.) ether, 25 deg C, 1 h, 2.) 10 h, 3.) 0 deg C, 1 h
9: triethylamine / 24 h / 25 °C
With
pyridine; hydrogenchloride; lithium aluminium tetrahydride; aluminium trichloride; hydrogen; sodium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; sodium iodide;
palladium on activated charcoal;
In
methanol; diethyl ether; dichloromethane;