triethylamine T=75°C; 4.5 h;

1: 90 percent / sodium azide, tetra-n-hexylammonium bromide / H2O / 2 h 2: 1.) Ph3P, 2.) H2O / 1) THF, 3 h, below 40 deg C, 20 deg C (1 h); 2) 1 h, 20 deg C 3: 57 percent / triethylamine / 4.5 h / 75 °C View Scheme

1: 1.) Ph3P, 2.) H2O / 1) THF, 3 h, below 40 deg C, 20 deg C (1 h); 2) 1 h, 20 deg C 2: 57 percent / triethylamine / 4.5 h / 75 °C View Scheme

1: 1.) H2O, 2.) aq. HCl / 1) reflux, 30 min; 2) reflux, 90 min 2: 86 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 18 h / 20 °C View Scheme