Multi-step reaction with 8 steps
1: 1.) s-BuLi, TMEDA, 2.) I2 / 1.) Et2O, cyclohexane, RT, 24 h, 2.) Et2O, cyclohexane, RT, 12 h
2: 93 percent / tri-o-tolylphosphine, palladium(II) acetate, Et3N / dimethylformamide / 0.5 h / 95 °C
3: ethanol. NaOH / 2 h / Heating
4: H2 / 10percent Pd-C / H2O / 4 h / 2585.7 - 2844.3 Torr / Ambient temperature
5: 9 percent / 3A molecular sieves / 50 h / Heating
6: 75 percent / diphenylphosphonic azide, Et3N / 24 h / Heating
7: ethanol. NaOH / 2 h / Heating
8: DCC / ethyl acetate / 14 h / Ambient temperature
With
sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; 3 A molecular sieve; diphenyl phosphoryl azide; hydrogen; iodine; sec.-butyllithium; palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; tris-(o-tolyl)phosphine;
palladium on activated charcoal;
In
water; ethyl acetate; N,N-dimethyl-formamide;