Multi-step reaction with 19 steps
1: 88 percent / NaOH/MeOH
2: 75 percent / 1.) HCl; 2.) K2CO3 / benzene / 1.) 30 min; 2.) 1 h
3: 76 percent / 1.) O3, pyridine; 2.) Me / CH2Cl2; methanol / 1.) -70 deg C; 2.) r.t., 3 h
4: 96 percent / lithium di-isopropylamide / tetrahydrofuran / 0.5 h / -70 °C
5: 35 percent / BF3*OEt2 / CH2Cl2 / 0.5 h / -70 °C
6: 100 percent / pyridine / 0.5 h / Ambient temperature
7: 40 percent / NaBH4 / 1,2-dimethoxy-ethane / 3 h / 0 °C
8: Et3N / dimethylformamide / 2 h / Ambient temperature
9: 1.) LiAlH4; 2.) 15percent aq. NaOH / diethyl ether / 0.67 h / Ambient temperature
10: 89 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 0.25 h
11: 1.) BuLi/hexane / 1.) THF, -78 deg C, 45 min; 2.) THF, -78 deg C, then r.t., 1 h
12: NaOH / dioxane / 4 h / Ambient temperature
13: 1.) Mg, 1,2-dibromethane; 2.) tris(acetonylacetonato)iron(III) / 1.) THF, r.t., 30 min, then reflux, 1 h; 2.) THF, r.t, 4 h
14: 98 percent / Na / liquid ammonia / 0.5 h / -70 °C
15: 94 percent / CrO3*2pyr / CH2Cl2 / 0.33 h
16: 1.) lithium di-isopropylamide; 2.) 3-dimethylaminopropylamine / 1.) THF, -70 deg C, 20 min; 2.) THF, r.t.
17: 51 percent / 5.65percent sodium amalgam, Na2HPO4 / tetrahydrofuran; methanol / 5.5 h / -20 °C
18: Et3N / CH2Cl2 / -10 °C
19: 1,5-diazabicyclo<4.3.0>non-5-ene / diethyl ether / 6 h / Heating
With
pyridine; hydrogenchloride; methanol; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; iron(III)-acetylacetonate; hexane; 3 A molecular sieve; boron trifluoride diethyl etherate; DBN; sodium; dipyridine chromium trioxide; potassium carbonate; ozone; magnesium; ethylene dibromide; triethylamine; 1-amino-3-(dimethylamino)propane; pyridinium chlorochromate; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; ammonia; N,N-dimethyl-formamide; benzene;