Multi-step reaction with 13 steps
1: NaBH3CN / acetic acid
2: cc. HCl / Heating
3: hydrogen / Pd(OH)2/C / acetic acid / 2068.6 Torr
4: AcOH / 16 h / 70 °C
5: 92 percent / NEt3, DCC / acetonitrile / 4 h / 60 °C
6: NEt3 / dimethylformamide
7: hydrogen / Pd/c / 2068.6 Torr
8: 1.) carbonyldiimidazol, 4-dimethylaminopyridine / 1.) CH2Cl2 2.) CH3CN, reflux
9: HCl / methanol; H2O
10: Triphenylphosphine, diisopropylazodicarboxylate, / THF, 25 deg C, 1 h
11: HCl / methanol; H2O / 1.5 h / 25 °C
12: TsN3, NEt3 / ethyl acetate
13: Rh2(OAc)4 / toluene / 1 h / 80 °C
With
hydrogenchloride; dmap; Carbonyldiimidazole; 4-toluenesulfonyl azide; di-isopropyl azodicarboxylate; hydrogen; sodium cyanoborohydride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine;
dirhodium tetraacetate; palladium dihydroxide; palladium on activated charcoal; acetic acid;
In
methanol; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)78606-0