N-ethyl-N,N-diisopropylamine in acetonitrile 1.) RT, 2.) reflux, 24 h;

in ethyl acetate; acetonitrile

1: H2 / W-2 Raney nickel / H2O; tetrahydrofuran / 2 h / 2068.6 Torr 2: NaHCO3 / H2O; tetrahydrofuran / 0.5 h 3: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min View Scheme

1: H2 / W-2 Raney nickel / H2O; tetrahydrofuran / 2 h / 2068.6 Torr 2: NaHCO3 / H2O; tetrahydrofuran / 0.5 h 3: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min 4: 99 percent / Et3N / CH2Cl2 / 2 h / Ambient temperature 5: 96 percent / NaN3 / dimethylformamide / 5 h / 65 °C 6: tetrahydrofuran / 2 h 7: H2O / 10 h / 40 °C 8: pyridine / CH2Cl2 / Ambient temperature View Scheme

Oxonetrade; in methanol; water T=20°C; 18 h;