Multi-step reaction with 14 steps
1: 46 percent / LiBH3(n-Bu) / toluene / 3 h / -78 °C
2: 91 percent / diisopropylethylamine / CH2Cl2 / 8 h / Ambient temperature
3: 95 percent / MeLi / diethyl ether / 0.08 h / 0 °C
4: pyridine / 12 h / 0 °C
5: 1) NaH / 1) DME, 0 deg C, 2) DME, 7h, reflux
6: 1) NaH, 2) Red-Al / 1) DME, RT, 30 min, 2) DME, toluene, 30 min, reflux
7: 78 percent / NaBH4, CoCl2*6H2O / ethanol / 24 h / Ambient temperature
8: 79 percent / pyridine / 2 h / 0 °C
9: 82 percent / SeO2, CaCO3 / xylene / 0.67 h / Heating
10: 88 percent / NaBH4 / methanol / 0.17 h / 0 °C
11: 90 percent / H2 / Raney Ni(W2) / ethanol / 2 h / 760 Torr / Ambient temperature
12: 82 percent / PCC, NaOAc / CH2Cl2 / 2 h / Ambient temperature
13: 68 percent / 3N HCl / tetrahydrofuran / 6 h / Ambient temperature
14: 1) NaI, 2) DBU / 1) DME RT, 2) reflux
With
pyridine; hydrogenchloride; sodium tetrahydroborate; selenium(IV) oxide; lithium [butyl(trihydrido)borate]; methyllithium; hydrogen; sodium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; calcium carbonate; sodium iodide; cobalt(II) chloride;
Raney Ni(W2);
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; xylene;
DOI:10.1248/cpb.38.361