hydrazine hydrate in tetrahydrofuran; ethanol 1) r.t., 16 h, 2) 70 deg C, 8 h;

1: 1) 2 N HCl, NaNO2, 2) NaN3 / 1) H2O, 30 min, 2) H2O, 3 h 2: 74 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 24 htmp 3: 92 percent / hydrazine hydrate / tetrahydrofuran; ethanol / 1) r.t., 16 h, 2) 70 deg C, 8 h View Scheme

1: 74 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 24 htmp 2: 92 percent / hydrazine hydrate / tetrahydrofuran; ethanol / 1) r.t., 16 h, 2) 70 deg C, 8 h View Scheme