Multi-step reaction with 10 steps
1: H2, AcOH / 5 percent Rh/C / 4 h / 50 °C
2: LAH / diethyl ether / 0 °C
3: Et3N / dimethylformamide / 1 h / 0 °C
4: NaN3 / dimethylformamide; H2O / 60 - 70 °C
5: H2O, Ph3P / tetrahydrofuran / Ambient temperature
6: HOBT, NMM, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
7: TFA / CH2Cl2 / 0 - 20 °C
8: HOBT, NMM, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 6.5 h / 0 - 20 °C
9: PPh3, i-Pr2NEt / acetonitrile; CCl4 / 16 h / Ambient temperature
10: NiO2, 4 Angstroem molecular sieves / benzene; dioxane / 4 h / Heating
With
4-methyl-morpholine; nickel(IV) oxide; lithium aluminium tetrahydride; sodium azide; 4 A molecular sieve; water; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid;
Rh on carbon;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jm980173n