Multi-step reaction with 8 steps
1: 82.5 percent / triethylamine / acetonitrile / Ambient temperature
2: triethylamine / CH2Cl2 / 1 h / 0 °C
3: NaOH / methanol; H2O / 2 h / Heating
4: 43 percent / acetic anhydride / 4 h / 90 °C
5: 1.) concd. HCl, 2.) p-TSA, H2O / 1.) ethanol, reflux, 24 h, 2.) acetone, reflux, 2 d
6: 1.) sodium hydride, n-butyllithium / 1.) THF, hexane, 0 deg C, 30 min, 2.)a) -78 deg C, 30 min, b) 0 deg C, 1 h
7: 1.) tributylborane, sodium borohydride, 2.) 3 N NaOH, 30percent H2O2 / 1.) THF, a) RT, b) 0 deg C, 3 h, 2.) RT
8: toluene / 6 h / Heating
With
hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; tributyl borane; water; dihydrogen peroxide; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; triethylamine;
In
methanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/jm00105a056