Multi-step reaction with 8 steps
1: 1.) n-BuLi / 1.) ether, hexane, -78 deg C, 30 min, 2.) ether, hexane, from -78 deg C to 0 deg C
2: 1.) N2H4*H2O, ethylene glycol, 2.) KOH / 1.) reflux, 45 min, 2.) reflux, 30 min
3: 83 percent / Pd(OAc)2, tri-o-tolylphosphine, Et3N / acetonitrile / 1 h / Heating
4: 95 percent / HCO2NH4 / 10percent Pd/C / ethanol; tetrahydrofuran / 1 h / 60 °C
5: 43 percent / aq. NaOH / ethanol / 0.75 h / Heating
6: diphenyl phosphorazidate, Et3N / 18 h / Heating
7: TFA / CH2Cl2 / 4 h / Ambient temperature
8: 4-(dimethylamino)pyridine, Et3N / CH2Cl2 / 2.5 h / Ambient temperature
With
dmap; palladium diacetate; potassium hydroxide; sodium hydroxide; n-butyllithium; diphenyl phosphoryl azide; ammonium formate; hydrazine hydrate; ethylene glycol; triethylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; acetonitrile;