Multi-step reaction with 12 steps
1: KOH / ethanol / 5 h / Heating
2: 41 percent / SOCl2 / CHCl3 / 0.75 h / Heating
3: 56 percent / Et3N / tetrahydrofuran / 0.25 h / 0 °C
4: 1.) LDA, LiCl / 1.) THF, hexane, a) -78 deg C, 1.75 h, b) 0 deg C, 20 min, c) 23 deg C, 5 min, 2.) THF, 0 deg C, 30 min
5: N-bromosuccinimide, glacial AcOH / tetrahydrofuran; H2O / a) 0 deg C, 15 min, b) reflux, 45 min
6: NaN3 / dimethylformamide / 67 h / 50 °C
7: H2 / 10 percent Pd/C / methanol / 16 h / 23 °C
8: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h / 23 °C
9: 4-methylmorpholine N-oxide, 4 A molecular sieves, tetrapropylammonium perruthenate / CH2Cl2 / 1.33 h / 23 °C
10: 4-methymorpholine, 1-hydroxybenzotriazole hydrate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / 2-methyl-propan-2-ol / 19 h / 23 °C
11: 4.0 M HCl / dioxane / 2 h / 23 °C
12: N,N-diisopropylethylamine / CH2Cl2 / 2 h / 23 °C
With
4-methyl-morpholine; hydrogenchloride; potassium hydroxide; lithium hydroxide; N-Bromosuccinimide; thionyl chloride; sodium azide; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; acetic acid; 4-methylmorpholine N-oxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jm980537b