Multi-step reaction with 7 steps
1: 1.) NaH / 1.) DMF, RT, 1.5 h, 2.) DMF, RT, overnight
2: 98.5 percent / 86percent KOH / ethanol / 2 h / Heating
3: 1.) SOCl2, 2.) NH3 (gas) / 1.) reflux, 3 h, 2.) THF, RT, 3 h
4: LiAlH4 / diethyl ether / a) RT, 10.5 h, b) reflux, 4 h
5: 75 percent / DCC, N-hydroxysuccinimide / dimethylformamide / a) -20 deg C, 2 h, b) RT, 2 h
6: 51 percent / CrO3 / acetic acid; H2O / Ambient temperature
7: 21.8percent HBr / acetic acid / 1.5 h / Ambient temperature
With
chromium(VI) oxide; potassium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; lithium aluminium tetrahydride; thionyl chloride; ammonia; hydrogen bromide; sodium hydride; dicyclohexyl-carbodiimide;
In
diethyl ether; ethanol; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jm00181a013