Multi-step reaction with 15 steps
1: dipyridinium dichromate / N,N-dimethyl-formamide / 12 h / 20 °C / Molecular sieve
2: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 - 20 °C
3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C
4: ammonia / methanol / 100 °C / Sealed tube
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
6: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran
7: hydrazine / ethanol / 80 °C
8: sodium cyanoborohydride; acetic acid / methanol / 0 °C
9: methanol / 65 °C
10: lithium aluminium tetrahydride / tetrahydrofuran / -15 °C
11: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran
12: hydrazine / ethanol / 80 °C
13: triethylamine / dichloromethane
14: hydrogenchloride / methanol
15: hydrogen; palladium 10% on activated carbon / methanol / 2 h / 20 °C
With
hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; ammonia; hydrogen; sodium cyanoborohydride; acetic acid; triethylamine; triphenylphosphine; hydrazine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c3md00021d