1: 2.) copper(I) iodide / 2.) THF, dimethylsulfide 2: NaH / tetrahydrofuran; dimethylformamide 3: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF 4: mesyl chloride, triethylamine / CH2Cl2 5: H2, HCl / 10 percent Pd/C / ethanol View Scheme

Multi-step reaction with 2 steps 1: 2.) copper(I) iodide / 2.) THF, dimethylsulfide2: NaH / tetrahydrofuran; dimethylformamide  

Multi-step reaction with 3 steps 1: 2.) copper(I) iodide / 2.) THF, dimethylsulfide2: NaH / tetrahydrofuran; dimethylformamide3: 1.) BH3; 2.) 30 percent H2O2, 12 percent NaOH / 1.) THF