Multi-step reaction with 11 steps
1: 95 percent / Cs2CO3 / dimethylformamide / 2 h / Ambient temperature
2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, -78 deg C, 5 min
3: CH2Cl2 / 0.5 h
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to 0 deg C
5: 1.) TiCl4 / 1.) Et2O, from -78 deg C to -35 deg C, 2.) Et2O, 0 deg C, 4 h
6: 81 percent / azidotrimethylsilane, BF3*OEt2 / CH2Cl2 / 120 h / Ambient temperature
7: H2 / 10 percent Pd/C / dimethylformamide / 24 h
8: HOBT, EDAC*HCl / dimethylformamide / 3.5 h / Ambient temperature
9: hydrazine hydrate / methanol; CH2Cl2 / 48 h / Ambient temperature
10: CH2Cl2 / 1.5 h / Ambient temperature
11: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 30 h / Ambient temperature
With
oxalyl dichloride; trimethylsilylazide; boron trifluoride diethyl etherate; hydrogen; titanium tetrachloride; benzotriazol-1-ol; caesium carbonate; hydrazine hydrate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm980542f