Multi-step reaction with 9 steps
1: H2, HClO4 / 10percent Pd/C / ethanol
2: 85 percent / H2 / Rh/Al2O3 / methanol / 4 h / 2327.2 Torr
3: NH2NH2, TEA / ethanol
4: I2, TEA / tetrahydrofuran
5: NH2NH2, O2, AcOH / ethanol / Heating
6: tris(trimethylsilyl)silane, AIBN / toluene / 90 °C
7: DBU / diethyl ether / 0 - 20 °C
8: 80 percent / NaBH4 / methanol; tetrahydrofuran / 1 h / Heating
9: 1.) LDA / 1.) THF, -20 deg C to 0 deg C, 1 h, 2.) THF, -78 deg C, 1.5 h
With
sodium tetrahydroborate; perchloric acid; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; TEA; hydrogen; iodine; oxygen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydrazine; lithium diisopropyl amide;
palladium on activated charcoal; Rh/Al2O3;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; toluene;
DOI:10.1055/s-1998-1902