Multi-step reaction with 9 steps
1: 81 percent / m-CPBA / CH2Cl2 / 36 h
2: TsOH*H2O / benzene; H2O / 24 h / Heating
3: 71 percent / Et3N, (PhO)2P(O)N3 / tetrahydrofuran / Ambient temperature
4: 84 percent / LiBH4 / methanol; tetrahydrofuran / 48 h / Ambient temperature
5: 84 percent / KH / tetrahydrofuran / 3 h / Ambient temperature
6: 70 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 2 h / Ambient temperature
7: 88 percent / CF3CO2H / CH2Cl2 / 10 h / -55 °C
8: 1.) BH3, 2.) 6 N NaOH, H2O2 / 1.) THF, room temperature, 2 h, 2.) EtOH, H2O, 55 deg C, 1.5 h
9: 97 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 1 h
With
sodium hydroxide; lithium borohydride; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; diphenyl phosphoryl azide; borane; dihydrogen peroxide; potassium hydride; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid;
In
tetrahydrofuran; methanol; dichloromethane; water; benzene;
DOI:10.1021/jo9707592