4-methyl-morpholine; dichlorotriphenylphosphorane in acetonitrile T=0°C; 0.833333 h;

1.1: N-methylmorpholine / tetrahydrofuran / 0.17 h / -10 °C 2.1: NaBH4 / methanol / 1.33 h / -78 - 0 °C 3.1: 89 percent / imidazole; DMAP / dimethylformamide / 20 °C 4.1: t-BuLi / tetrahydrofuran; pentane / -100 °C 4.2: 61 percent / trisyl azide / tetrahydrofuran; pentane / -100 - 20 °C 5.1: 100 percent / TBAF / tetrahydrofuran / 20 °C 6.1: 20 percent / PPh3Cl2; N-methylmorpholine / acetonitrile / 0.83 h / 0 °C View Scheme

1.1: 89 percent / imidazole; DMAP / dimethylformamide / 20 °C 2.1: t-BuLi / tetrahydrofuran; pentane / -100 °C 2.2: 61 percent / trisyl azide / tetrahydrofuran; pentane / -100 - 20 °C 3.1: 100 percent / TBAF / tetrahydrofuran / 20 °C 4.1: 20 percent / PPh3Cl2; N-methylmorpholine / acetonitrile / 0.83 h / 0 °C View Scheme

1: 100 percent / TBAF / tetrahydrofuran / 20 °C 2: 20 percent / PPh3Cl2; N-methylmorpholine / acetonitrile / 0.83 h / 0 °C View Scheme