Multi-step reaction with 5 steps
1: 1.) lithium diisopropylamide / 1.) THF, hexane, HMPA, -78 deg C, 2.5 h, 2.) -78 deg C, 5 h, room temperature, 15 h
2: 1.) lithium diisopropylamide / 1.) THF, hexane, HMPA, -78 deg C, 7 h, 2.) -78 deg C, 5 h, room temperature, 15 h
3: 63 percent / hydrogen / 5percent palladium on carbon / acetic acid; ethanol / 15 h / 1810.02 Torr
4: 100 percent / n-butyllithium / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.) room temperature, 2 h
5: 90 percent / sodium azide / dimethylformamide / 12 h / 80 °C
With
n-butyllithium; sodium azide; hydrogen; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; hexane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/ja00348a051