Multi-step reaction with 10 steps
1: H2 / Pd/C / ethanol / 2 h / 23 °C / 62057.8 Torr
2: 1.) aq. NaNO2, HCl, 2.) NaN3 / 1.) EtOH, 0 deg C, 20 min, 2.) EtOH, 0 deg C, 40 min
3: i-Pr2NEt / CH2Cl2 / 23 °C
4: NBS, Bz2O2 / benzene / 2 h / Heating
5: K2CO3 / dimethylformamide / 0.25 h / 70 °C
6: TFA / CH2Cl2 / 3 h / 23 °C
7: K2CO3 / dimethylformamide / 80 °C
8: 100 percent / DIBAL / CH2Cl2 / -78 °C
9: 98 percent / PCC / CH2Cl2 / 23 °C
10: toluene / 7 h / 170 °C
With
hydrogenchloride; N-Bromosuccinimide; sodium azide; hydrogen; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; trifluoroacetic acid; sodium nitrite; dibenzoyl peroxide;
palladium on activated charcoal;
In
ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja00027a071