Multi-step reaction with 8 steps
2: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 10 min
3: BH3*Me2S / tetrahydrofuran / 1 h
4: imidazole / dimethylformamide
5: NaOMe / methanol / 0.25 h / 0 °C
6: 1.) LiN(TMS)2, 2.) ethyl(dimethylaminoethyl) carbodiimide HCl, DMAP / 1.) THF, 0 deg C, then 25 deg C, 2.) Et2O
7: 1.) NaIO4, 2.) pyr. / 1.) H2O, 2.) toluene, reflux, 3 h
8: H2 / Pd/C / ethyl acetate
With
pyridine; 1H-imidazole; dmap; sodium periodate; dimethylsulfide borane complex; hydrogen; sodium methylate; 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)80903-5