Multi-step reaction with 9 steps
1: N,N-dimethylaniline / bis-(2-methoxy-ethyl) ether / 10 h / 160 °C
2: K2CO3 / dimethylformamide / 8 h / 70 - 75 °C
3: 1.) 9-BBN, 2.) 2N aq. NaOH, H2O2 / 1.) THF, a) 25 deg C, 30 min, b) reflux, 90 min, 2.) THF, reflux, 1 h
4: pyridine / CH2Cl2 / 6 h / 20 °C
5: NaI / acetone / 4 h / Heating
6: dimethylsulfoxide / 4 h / 60 °C
7: H2, conc. HCl / 10percent Pd/C / acetic acid / 0.33 h / 25 °C / 750.06 Torr
8: 94 percent / H2 / 10percent Pd/C / ethyl acetate / 12 h / 750.06 Torr
9: K2CO3, hydroquinone / dimethylsulfoxide / 3 h / 70 °C
With
pyridine; hydrogenchloride; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; dihydrogen peroxide; potassium carbonate; N,N-dimethyl-aniline; hydroquinone; sodium iodide;
palladium on activated charcoal;
In
dichloromethane; diethylene glycol dimethyl ether; acetic acid; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm00114a004