1: 85 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature 2: 59 percent / tributyl-tin hydride, AIBN / toluene / 1.5 h / Heating View Scheme

With  L-Selectridereg; in  dichloromethane T=-78°C; 0.25 h;   

Multi-step reaction with 2 steps 1: 1.) sodium hydride; 2.) lithium iodide / 1.) dioxan, ethanol, 15 min; 2.) dimethylformamide, reflux, 4.5 h2: 97 percent / L-selectride / CH2Cl2 / 0.25 h / -78 °C  

Multi-step reaction with 4 steps 1: CH2Cl2; methanol / 15 h / Ambient temperature2: 96 percent / Huenig base / acetonitrile / 3 h / Heating3: 1.) sodium hydride; 2.) lithium iodide / 1.) dioxan, ethanol, 15 min; 2.) dimethylformamide, reflux, 4.5 h4: 97 percent / L-selectride / CH2Cl2 / 0.25 h / -78 °C  

Multi-step reaction with 5 steps 1: 49 percent / tetraethylammonium-tetrahydridoborate / CH2Cl2 / 0.5 h2: CH2Cl2; methanol / 15 h / Ambient temperature3: 96 percent / Huenig base / acetonitrile / 3 h / Heating4: 1.) sodium hydride; 2.) lithium iodide / 1.) dioxan, ethanol, 15 min; 2.) dimethylformamide, reflux, 4.5 h5: 97 percent / L-selectride / CH2Cl2 / 0.25 h / -78 °C