Multi-step reaction with 10 steps
1: 97 percent / hydrazine hydrate / dioxane / 1 h / Ambient temperature
2: 63 percent / tetrahydrofuran / 1 h / Heating
3: 1.) ozone 2.) dimethyl sulfide / 1.) CH2Cl2, -70 deg C 2.) CH2Cl2, 1 h, room temp.
4: 91 percent / acetic acid, sodium cyanoborohydride / tetrahydrofuran / 1 h / Ambient temperature
5: 72 percent / pyridine / 24 h / Ambient temperature
6: lithium bis(trimethylsilylamide) / tetrahydrofuran; toluene / 1 h / Ambient temperature
7: CH2Cl2 / 0.5 h / Ambient temperature
8: 40 percent / hydrogen, / 10percent palladium on charcoal / tetrahydrofuran; methanol / 15 h / 1520 Torr
9: trimethylsilyl trifluoromethanesulfonate / CH2Cl2 / 0.25 h / 0 °C
10: 1.) tosylchloride 2.) triethylamine, KOH / 1.) acetone, 1 h, room temp. 2.) CH2Cl2, 2 h, room temp.
With
pyridine; potassium hydroxide; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium cyanoborohydride; ozone; hydrazine hydrate; acetic acid; triethylamine; p-toluenesulfonyl chloride; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene;