Multi-step reaction with 8 steps
1: 94 percent / Et3N / CH2Cl2 / 20 h / 0 °C
2: 98 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h / 70 °C
3: 76 percent / NaNO3, La(NO3)3*6H2O, conc. aq. HCl / diethyl ether / 3 h / Ambient temperature
4: 81 percent / diethylazodicarboxylate, PPh3 / diethyl ether / 48 h / Ambient temperature
5: 98 percent / KOH / ethanol / 3 h / 50 °C
6: 78 percent / dicyclohexylcarbodiimide, 4-(dimethylaminopyridine) / CH2Cl2 / 48 h
7: 1.) 9-BBN, 2.) 30percent aq. H2O2 / 1.) THF, 3 h, 2.) THF, EtOH, 50 deg C, 1 h
8: 33 percent / Et3N / tetrahydrofuran / 12 h / 0 °C
With
hydrogenchloride; dmap; potassium hydroxide; sodium nitrate; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; dihydrogen peroxide; lanthanum(III) nitrate; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate;
DOI:10.1021/ja961309e