Multi-step reaction with 8 steps
1: 99 percent / pyridine / CH2Cl2 / 1 h / 0 °C
2: 1.) LiCl, PdCl
26H5)3>2 / 1.) DMF, RT, 15 min, 2.) DMF, RT, 12 h
3: 1.) 9-BBN, 2.) aq. H2O2 / 1.) THF, RT, 48 h, 2.) THF, from 0 deg C to RT, 2 h
4: CrO3, H2SO4 / acetone / 38 h / 0 °C
5: CH2Cl2 / 1 h / Ambient temperature
6: 4-(dimethylamino)pyridine / CH2Cl2 / 18 h / Ambient temperature
7: 90 percent / H2 / 10percent Pd/C / ethanol / 2.5 h / 1810.02 Torr
8: K2CO3 / butan-2-one / 18 h / Heating
With
pyridine; chromium(VI) oxide; dmap; bis-triphenylphosphine-palladium(II) chloride; 9-borabicyclo[3.3.1]nonane dimer; sulfuric acid; hydrogen; dihydrogen peroxide; potassium carbonate; lithium chloride;
palladium on activated charcoal;
In
ethanol; dichloromethane; acetone; butanone;
DOI:10.1021/jm950699x