Multi-step reaction with 5 steps
1: triethylamine / tetrahydrofuran / 0.58 h / -15 - 0 °C
2: 1.) n-butyllithium / 1.) THF, hexane, - 60 deg C, 2.) THF, hexane, -78 deg C, 1 h
3: 1.) potassium bis(trimethylsilyl)amide, 2.) 2,4,6-triisopropylbenzenesulfonyl azide / 1.) THF, toluene, -78 deg C, 30 min, 2.) THF, toluene, -75 deg C, 2 min
4: aq. LiOH / tetrahydrofuran / 0.75 h / Ambient temperature
5: 270 mg / H2 / 5percent Pd/C / ethanol; H2O / 24 h
With
lithium hydroxide; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; water;
DOI:10.1021/jm00068a006