Multi-step reaction with 8 steps
1: 1.) 9-borabicyclo<3.3.1>nonane, 2.) aq. NaOH, H2O2
2: 2.) dibenzylammonium trifluoroacetate / 1.) by Swern oxidation, 2.) benzene, 70 deg C
3: 88 percent / diisobutylaluminum hydride / toluene; hexane / 1.5 h / -78 °C
4: 99 percent / 4-dimethylaminopyridine / pyridine / 0.5 h / 23 °C
5: 1.) cuprous iodide, 2.) 9-borabicyclo<3.3.1>nonane, 3.) 6 N aq. NaOH, 30 percent H2O2 / 1.) ether/hexane, -78 deg C, 1h then 23 deg C, 20 min, 2.) THF, 0 deg C, 3 h then 23 deg C, 1 h, 3.) THF, 50 deg C, 1 h
6: 87 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 2 h / 23 °C
7: 77 percent / silver oxide, AgNO3, 5 N aq. NaOH / methanol; tetrahydrofuran / 0.42 h / 45 °C
8: tetra-n-butylammonium fluoride / tetrahydrofuran / 48 h / 23 °C
With
sodium hydroxide; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium acetate; diisobutylaluminium hydride; silver nitrate; pyridinium chlorochromate; silver(l) oxide; dibenzylammonium trifluoroacetate salt;
dmap;
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; toluene;
DOI:10.1248/cpb.37.586