Multi-step reaction with 15 steps
1: 51 percent / NaH, CuBr*S(CH3)2 / nitrobenzene / 8 h / 130 °C
2: 89 percent / BH3*THF / tetrahydrofuran / 3 h / 0 °C
3: 72 percent / CBr4, (C6H5)3P / diethyl ether / 25 °C
4: 1.) NaH / 1.) THF, 0 deg C, 5 min, 2.) -78 deg C, 14 h
5: 0.5 N aq. HCl / tetrahydrofuran / 15 h / 25 °C
6: 97 percent / tetrahydrofuran / 1 h / 25 °C
7: 68 percent / NaH / tetrahydrofuran / 0 - 25 °C
8: 86 percent / K2CO3 / methanol; H2O / 6 h / 25 °C
9: 91 percent / K2CO3 / tetrahydrofuran / 2 h / 25 °C
10: 85 percent / EDCI / CH2Cl2 / 9 h / 25 °C
11: 92 percent / n-Bu4NF / dimethylformamide / 4 h / 25 °C
12: 85 percent / EDCI / CH2Cl2 / 2 h / 25 °C
13: H2, 10percent aq. HCl / 10percent Pd/C / tetrahydrofuran / 4 h / 25 °C / 760 Torr
14: NaHCO3 / dimethylformamide / 2 h / 90 °C
15: 1.) 3.0 M HCl, 2.) NaHCO3 / 1.) EtOAc, 25 deg C, 2 h, 2.) THF, 25 deg C, 2 h
With
hydrogenchloride; borane-THF; copper(I) bromide dimethylsulfide complex; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; nitrobenzene; N,N-dimethyl-formamide;
DOI:10.1021/jo00272a003
