Multi-step reaction with 11 steps
1: 68 percent / H2 / Pd/C / ethanol / 2 h
2: 97 percent / I2, KI, NaHCO3 / ethanol; H2O / 1 h / Heating
3: 74 percent / H2, NaOAc / Pd/C / methanol / 2 h / 2585.7 Torr
4: 80 percent / p-TsOH / CHCl3 / 2 h / Heating
5: 66 percent / B2H6 / tetrahydrofuran / 26 h / 25 °C
6: 74 percent / KOH / ethanol; H2O / 110 °C
7: 62 percent / pyridine / 2 h / 25 °C
8: 1.) p-TsOH / 1.) CH2Cl2, MeOH, 25 deg C, 72 h, 2.) Py, 2 h
9: 90 percent / aq. H2SO4 / methanol / 24 h / 25 °C
10: 52 percent / mesyl chloride / dimethylformamide / 18 h / 75 °C
11: 72 percent / aq. KOH / pyridine / 3 h / Heating
With
potassium hydroxide; sulfuric acid; hydrogen; iodine; sodium acetate; sodium hydrogencarbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; potassium iodide; diborane;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jo971807l