Multi-step reaction with 18 steps
1: 18.74 g / DMAP, Et3N / CH2Cl2 / Ambient temperature
2: 13.90 g / AD-mix-β, MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 10 h / 0 °C
3: Amberlyst 15 / 4 h
4: 4.32 g / K2CO3 / methanol; H2O / Ambient temperature
5: 93 percent / CBr4, PPh3 / CH2Cl2 / 1 h / Ambient temperature
6: 73 percent / toluene / 60 h
7: 100 percent / HCl / H2O; tetrahydrofuran / 0.5 h
8: H2 / Pd/C / methanol / 0.5 h
9: 1.97 g / Et3N / methanol / 2 h / Ambient temperature
10: Et3N / CH2Cl2 / 2 h / Ambient temperature
11: 3.71 g / NaN3 / dimethylformamide / 20 h / 85 - 90 °C
12: 100 percent / H2 / Pd/C / methanol / 8 h
13: 41 percent / CH2Cl2; triethylamine / 8 h / Ambient temperature
14: 100 percent / i-Pr2NEt / tetrahydrofuran / Ambient temperature
15: H2 / Pd/C / methanol / 3 h
16: 78 percent / i-Pr2NEt / tetrahydrofuran / Ambient temperature
17: NaOH / tetrahydrofuran; methanol / 4 h / Ambient temperature
18: 79 mg / pyridine; dimethylformamide / 4 h / Ambient temperature
With
hydrogenchloride; dmap; sodium hydroxide; sodium azide; Amberlyst 15; carbon tetrabromide; methanesulfonamide; AD-mix-β; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; water; triethylamine; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/S0040-4020(97)90388-4