Multi-step reaction with 9 steps
1: 1.) LDA, HMPA / 1.) THF, hexane, a) 0-5 deg C, 6 h, b) RT temp., 22 h, 2.) 0-5 deg C
2: 28 percent / NaHCO3 / dimethylformamide / 72 h / Ambient temperature
3: 97 percent / 1N HCl / acetic acid / 18 h / Ambient temperature
4: K2CO3 / 0.67 h / 60 °C
5: Et3N / tetrahydrofuran / 1.) -20 deg C, 2.) RT, 15 h
6: 73 percent / conc. NH4OH / methanol / 72 h / Ambient temperature
7: 1.) Na, 2.) H2O / 1.) 2-methoxyethanol, 115-120 deg C, 24 h, 2.) 100 deg C, 4 h
8: 94 percent / 10percent NaOH / 2.5 h / Heating
9: 39 percent / ET3N, isobutyl chloroformate / dimethylsulfoxide / 20 h / Ambient temperature
With
hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; ammonium hydroxide; sodium hydroxide; water; sodium; sodium hydrogencarbonate; potassium carbonate; triethylamine; lithium diisopropyl amide; isobutyl chloroformate;
In
tetrahydrofuran; methanol; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm00164a033