triethylamine T=19 - 20°C; 1 h;

1: 93.4 percent / LiAlH4 / diethyl ether / 0.5 h / Heating 2: 95 percent / triethylamine / 1 h / 19 - 20 °C View Scheme

1: 93.4 percent / LiAlH4 / diethyl ether / 0.5 h / Heating 2: 95 percent / triethylamine / 1 h / 19 - 20 °C View Scheme

(i) BH3, THF, (ii) /BRN= 1306669/; Multistep reaction;

N,N'-dimethyl-N,N'-propyleneurea in tetrahydrofuran T=20°C; 24 h; Title compound not separated from byproducts;

sodium iodide in acetone 2 h; Heating;

1: 92.2 percent / NaI / acetone / 2 h / Heating 2: 1.) Na; 2.) 3 N H2SO4 / 1.) ether, xylene, 35 -40 deg C, 10 h View Scheme

1: 87 percent / 156 °C 2: 98 percent / aq. H2SO4 / acetone / 0.5 h / 20 °C View Scheme

1: 92.2 percent / NaI / acetone / 2 h / Heating 2: 1.) Na; 2.) 3 N H2SO4 / 1.) ether, xylene, 35 -40 deg C, 10 h 3: 93.8 percent / 48percent HBr / H2O; cyclohexane / 48 h / 80 °C 4: 98.6 percent / p-toluenesulfonic acid / diethyl ether / 2 h / 19 - 20 °C 5: 86.6 percent / Na / H2O; xylene; diethyl ether 6: 85.1 percent / p-toluenesulfonic acid / methanol / 2 h / Heating View Scheme