hydrogenchloride; hydrogen; palladium on activated charcoal in ethanol Yield given;

Multi-step reaction with 12 steps 1: OsO4 2: p-TsOH / acetone3: H2 / Pd black / methanol4: borane, dimethylsulfide / tetrahydrofuran5: N,N-diethylaniline6: 10 percent HCl / methanol / 40 °C7: NaH / tetrahydrofuran; dimethylformamide8: 10 percent HCl / methanol / 70 °C9: 2.) copper(I) iodide / 2.) THF, dimethylsulfide10: NaH / tetrahydrofuran; dimethylformamide11: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF12: mesyl chloride, triethylamine / CH2Cl2  

Multi-step reaction with 13 steps 1: p-TsOH / acetone2: 1.) LiAlH4; 2.) pyridine; 3.) NaN3 / 1.) THF; 3.) DMF, 130 deg C3: 65 percent / H2 / Pd black / ethanol4: K2CO3 / ethanol5: cc. HCl / methanol6: N,N-diethylaniline7: 10 percent HCl / methanol / 40 °C8: NaH / tetrahydrofuran; dimethylformamide9: 10 percent HCl / methanol / 70 °C10: 2.) copper(I) iodide / 2.) THF, dimethylsulfide11: NaH / tetrahydrofuran; dimethylformamide12: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF13: mesyl chloride, triethylamine / CH2Cl2  

Multi-step reaction with 12 steps 1: 1.) LiAlH4; 2.) pyridine; 3.) NaN3 / 1.) THF; 3.) DMF, 130 deg C2: 65 percent / H2 / Pd black / ethanol3: K2CO3 / ethanol4: cc. HCl / methanol5: N,N-diethylaniline6: 10 percent HCl / methanol / 40 °C7: NaH / tetrahydrofuran; dimethylformamide8: 10 percent HCl / methanol / 70 °C9: 2.) copper(I) iodide / 2.) THF, dimethylsulfide10: NaH / tetrahydrofuran; dimethylformamide11: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF12: mesyl chloride, triethylamine / CH2Cl2  

Multi-step reaction with 11 steps 1: p-TsOH / acetone2: H2 / Pd black / methanol3: borane, dimethylsulfide / tetrahydrofuran4: N,N-diethylaniline5: 10 percent HCl / methanol / 40 °C6: NaH / tetrahydrofuran; dimethylformamide7: 10 percent HCl / methanol / 70 °C8: 2.) copper(I) iodide / 2.) THF, dimethylsulfide9: NaH / tetrahydrofuran; dimethylformamide10: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF11: mesyl chloride, triethylamine / CH2Cl2