1: pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 2: 78 percent / sodium borohydride / ethanol / 1 h / 0 °C 3: 1.) aq. trifluoroacetic acid; 2.) sodium brohydride / 1.) room temp., 30 min.; 2.) aq. ethanol, room temp., 15 min. 4: hydrogen / palladium black / acetic acid / 48 h View Scheme

2: NaN3 / dimethylformamide / 48 h / 70 °C 3: 1.) H2 / 1.) palladium black, ethanol; 2.) pyridine 4: 2.) sodium borohydride 5: H2 / palladium black / acetic acid View Scheme

With  pyridinium chlorochromate in  dichloromethane 2 h;  Ambient temperature;   

Multi-step reaction with 2 steps 1: pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature2: 78 percent / sodium borohydride / ethanol / 1 h / 0 °C  

With  pyridine in  dichloromethane T=-30°C; 0.5 h;   

Multi-step reaction with 3 steps 1: pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature2: 78 percent / sodium borohydride / ethanol / 1 h / 0 °C3: 1.) aq. trifluoroacetic acid; 2.) sodium brohydride / 1.) room temp., 30 min.; 2.) aq. ethanol, room temp., 15 min.