Multi-step reaction with 10 steps
1: 90 percent / 70percent perchloric acid, hydrogen / 5percent palladium-charcoal / acetic acid / 1.5 h / 70 °C
2: triethylamine / CH2Cl2 / 1 h / -5 °C
3: sodium iodide / acetone / 2 h / 50 °C
4: 1.) sodium amide / 1.) Et2O, liquid ammonia, -50 deg C - -40 deg C, 60 min, 2.) -50 deg C - -40 deg C, 100 min
5: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C
6: triethylamine / CH2Cl2 / 1 h / -5 °C
7: sodium iodide / acetone / 2 h / 50 °C
8: 1.) ethyl magnesium bromide, 2.) copper(I) bromide / 1.) THF, 2.) 50 deg C, 2 h
9: toluene-p-sulphonic acid / methanol / 0.5 h / 70 °C
10: 72 percent / pyridine-2,6-dicarboxylic acid, cerium(IV) ammonium nitrate / acetonitrile; H2O / 0.5 h / 0 - 2 °C
With
perchloric acid; Pyridine-2,6-dicarboxylic acid; ammonium cerium(IV) nitrate; ethylmagnesium bromide; hydrogen; toluene-4-sulfonic acid; sodium amide; triethylamine; sodium iodide; copper(I) bromide;
palladium on activated charcoal;
In
methanol; dichloromethane; water; acetic acid; acetone; acetonitrile;