Multi-step reaction with 10 steps
1: 84 percent / N-formyl-piperidine / 64 h / 160 - 170 °C
2: tetrahydrofuran; toluene / 3 h / Heating
3: 4N aq. HCl / toluene; tetrahydrofuran / 20 °C
4: 23 percent / diethyl ether / 1.) 40 deg C, 5 h, 2.) RT, 5 d
5: 96 percent / H2 / 10 percent Pd/C / ethanol / 750.06 Torr / Ambient temperature
6: 1.) NaOEt / 1.) EtOH, 50 deg C, 2.) EtOH, a) reflux, 2 h, b) RT, overnight
7: H2SO4 / 0.08 h / 80 °C
8: aq. H2SO4 / 1 h / 110 °C
9: 88 percent / p-TsOH*H2O / benzene / 72 h / Heating
10: 1.) n-BuLi / 1.) Et2O, hexane, 25 deg C, 30 min, 2.) Et2O, hexane, RT, overnight
With
N-Formylpiperidine; hydrogenchloride; n-butyllithium; sulfuric acid; hydrogen; sodium ethanolate; toluene-4-sulfonic acid;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; toluene; benzene;
DOI:10.1021/jm9810349