sodium hydride 1.) DME, r.t., 24 h; 2.) DME, r.t., 24 h; Yield given. Multistep reaction;

1: Et3N / CH2Cl2 / 18 h / Ambient temperature 2: NaN3 / dimethylformamide / 3 h / 80 °C 3: Lindlar catalyst, H2 / ethyl acetate / 6 h / 30 °C / 2327.2 Torr 4: 1.) 1-hydroxybenzotriazole hydrate, N,N'-dicyclohexylcarbodiimide / 1.) EtOAc, RT, 2 h, 2.) 18 h 5: 89 percent / H2 / Pearlman's catalyst / ethanol / 18 h / 25 °C / 2327.2 Torr 6: 80 percent / ethyl acetate / 24 h / Ambient temperature View Scheme