Multi-step reaction with 10 steps
1: 1.) KN(TMS)2, 2.) BF3*Et2O / 1.) THF, -78 deg C, 15 min, 2.) -78 deg C, 1.5 h
2: 88 percent / pyridine / CH2Cl2 / 48 h / 20 °C
3: 93 percent / NaN3 / dimethylformamide / 20 h / 40 °C
4: 1 M aq. NaOH / methanol / 48 h / 20 °C
5: H2, 2 M aq. HCl / 10percent Pd/C / ethanol / 2 h / 20 °C / 2844.3 Torr
6: dioxane / 4 h / 55 °C
7: Et3N / dioxane / 35 °C
8: 1 N aq. HCl / methanol; dioxane
9: 72 percent / DPPA, Et3N / dimethylformamide / 6 h / 0 °C
10: 54 percent / Me3SiI / acetonitrile / 0.25 h / 20 °C
With
pyridine; hydrogenchloride; sodium hydroxide; sodium azide; trimethylsilyl iodide; boron trifluoride diethyl etherate; diphenyl-phosphinic acid; hydrogen; potassium hexamethylsilazane; triethylamine;
palladium on activated charcoal;
In
1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00104a022