Multi-step reaction with 12 steps
1: aq. NaOH / ethanol / 3 h / 70 °C
2: HOBt; EDC*HCl; NMM / CH2Cl2 / 0 - 20 °C
3: 71 percent / AcOH / H2O / 96 h / 65 °C
4: 91 percent / 2,6-lutidine / CH2Cl2 / -78 - 0 °C
5: 82 percent / NaH / dimethylformamide / 14 h / 0 - 20 °C
6: 78 percent / Super-hydride / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C
7: 87 percent / tetrahydrofuran / -78 °C
8: BCl3*DMS / CH2Cl2 / 24 h / 0 - 20 °C
9: HF; H2O / acetonitrile / 22 h / 20 °C
10: CAN / acetonitrile; H2O / 1 h / 0 °C
11: [MeTeAlMe2]2 / toluene / 24 h / 20 °C
12: BOP-Cl; pyridine / CH2Cl2 / 3 h / 20 °C
With
4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; sodium hydroxide; ammonium cerium(IV) nitrate; boron trichloride - methyl sulfide complex; hydrogen fluoride; water; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydride; lithium triethylborohydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1039/b607109k