Multi-step reaction with 8 steps
1: 90 percent / 1 N aq. NaOH / CH2Cl2 / a) 0 deg C, 4 h, b) RT, 1 h
2: 1.) lithium diisopropylamide / 1.) THF, 0 deg C, 30 min, 2.) THF, a) 0 deg C, 5 h, b) -15 deg C, 15 h
3: 36 percent / 1 N ethanolic HCl / 15 h / Heating
4: 91 percent / H2 / 5percent Pd/C / ethanol / 3 h / 2068.6 Torr / Ambient temperature
5: 76 percent / pyridinium dichromate / dimethylformamide / 15 h / Ambient temperature
6: 97 percent / oxalyl chloride / CH2Cl2 / 2.5 h / Ambient temperature
7: 85 percent / pyridine / 3 h / Ambient temperature
8: 80 percent / 1 N aq. LiOH / methanol / 6 h / 55 °C
With
pyridine; hydrogenchloride; lithium hydroxide; sodium hydroxide; dipyridinium dichromate; oxalyl dichloride; hydrogen; lithium diisopropyl amide;
palladium on activated charcoal;
In
methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00363a012