Multi-step reaction with 7 steps
1: n-BuLi, hexamethylphosphoramide / tetrahydrofuran / 1 h / 0 °C
2: p-TsOH / methanol / 25 °C
3: H2 / Pd/CaCO3, Pb / ethyl acetate / 10 h / 25 °C
4: 1.) NaH / 1.) THF, from 0 deg C to RT, 35 min, 2.) THF, 25 deg C, 12 h
5: 98 percent / 50percent aq. HF / acetonitrile / 0.25 h / Ambient temperature
6: 93 percent / Ph3P, imidazole, I2 / diethyl ether; acetonitrile / 1 h / 25 °C
7: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 1 h
With
1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; hydrogen fluoride; hydrogen; iodine; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; lithium diisopropyl amide;
Lindlar's catalyst; Piperonyl butoxide;
In
tetrahydrofuran; methanol; diethyl ether; ethyl acetate; acetonitrile;
DOI:10.1021/jm9606047