Multi-step reaction with 7 steps
1: 62 percent / BF3*Et2O / CH2Cl2 / 16 h / 0 °C
2: Dibal-H / toluene / -78 °C
3: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 0.5 h, 2.) THF, hexane, from -78 deg C to 0 deg C, 1 h
4: 1.) dicyclohexylborane, 2.) H2O2 / 1.) THF, 0.5 h, 2.) THF, MeOH, 0.5 h
5: 89 percent / DCC, 1-hydroxybenzotriazole hydrate / dimethylformamide / 2.5 h / -23 - 23 °C
6: H2 / 5percent Pd/C / ethanol / 258.6 Torr
7: 6.5N aq. HCl / CH2Cl2; dioxane / 0.17 h / 23 °C
With
hydrogenchloride; n-butyllithium; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00080a005