Multi-step reaction with 11 steps
1: 67 percent / hexamethylenetetramine / acetic acid; H2O / 1 h / 120 °C
2: 1.) NaH; 2.) NaH, I2 / 1.) DME, 0 degC; 2.) 25-40 degC
3: Li2CO3 / dimethylformamide / 16 h / 80 °C
4: NaBH4 / methanol / 1 h / -10 °C
5: NaHTe / ethanol / 3 h / Ambient temperature
6: 1.) Im; 2.) NaBH4, CaCl2 / 1.) DMF, room t., 3 h; 2.) i-PrOH, room t., 22 h
7: 94 percent / Im / dimethylformamide / Ambient temperature
8: 69 percent / HCOOH-H2O / tetrahydrofuran / 18 h / Ambient temperature
9: 96 percent / triethylamine, (COCl)2 / dimethylsulfoxide; CH2Cl2 / -78 °C
10: 56 percent / tetrahydrofuran / 0.5 h / -78 °C
11: 64 percent / HgCl2, HCl / H2O / 17 h / Heating
With
hydrogenchloride; sodium tetrahydroborate; formic acid; oxalyl dichloride; sodium hydrogen telluride; hexamethylenetetramine; impramine; iodine; lithium carbonate; sodium hydride; triethylamine; calcium chloride; mercury dichloride;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)78550-9