Multi-step reaction with 13 steps
1: Cr-salen complex / 24 h / -10 °C
2: TFA / methanol / Ambient temperature
3: TBHP / Mo(CO)6 / benzene / Heating
4: KH / tetrahydrofuran / 0 °C
5: 94 percent / NaBH4 / ethanol
6: 1.) H2O2, NaHCO3, 2.) iPrNH2 / 1.) THF, 2.) benzene, reflux
7: 97 percent / TEMPO, NaOCl / CH2Cl2
8: H2NOH*HCl, pyridine / CH2Cl2
9: Et3N / CH2Cl2
10: 1.) TiCl3(OiPr), 2.) KH / 1.) CH2Cl2, rt, 2.) THF
11: 87 percent / AlH3 / tetrahydrofuran / 0 °C
12: H2 / PtO2 / ethyl acetate
13: Et3N / CH2Cl2 / 0 deg C to rt
With
pyridine; aluminium hydride; tert.-butylhydroperoxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; titanium(IV) trichloride isopropoxide; hydroxylamine hydrochloride; hydrogen; dihydrogen peroxide; potassium hydride; sodium hydrogencarbonate; isopropylamine; triethylamine; trifluoroacetic acid;
platinum(IV) oxide; hexacarbonyl molybdenum; Cr-salen;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; benzene;
DOI:10.1016/S0040-4039(97)00192-5