Multi-step reaction with 11 steps
1: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h
2: H2 / 10percent Pd/C
3: 1N aq. NaOH / ethanol / 3 h / Ambient temperature
4: 97 percent / NaBH4, BF3*Et2O / tetrahydrofuran / Ambient temperature
5: 45 g / triethylamine / CH2Cl2 / 1 h
6: 95 percent / NaI / acetone / 12 h / Heating
7: 19 percent / tributyltin hydride, AIBN / benzene / 0.33 h / Heating
8: 89 percent / N,N-diisopropylethylamine / hexane / 5 h / Ambient temperature
9: 78 percent / 2-methyl-propan-2-ol / 12 h / 160 °C
10: 100 percent / 1N HCl / acetic acid / 2 h / Ambient temperature
11: DPPA, Et3N / dimethylformamide / 1.) ice-bath cooling, 30 min, 2.) RT, 2 h
With
hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; diphenyl-phosphinic acid; hydrogen; tri-n-butyl-tin hydride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/jm00037a012