Multi-step reaction with 15 steps
1: 92 percent / acetic anhydride / 6 h / Heating
2: 83 percent / p-TsOH, HC(OEt)3 / 1 h / Heating
3: 88 percent / NaBH4 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 5 h / 0 deg C to room temp.
4: 95 percent / pyridine / 4 h / Ambient temperature
5: 1.) PCC; 2.) Li/liq. NH3 / 1.) CH2Cl2, room temp., 2 h; 2.) dioxane, MeOH, -30 deg C
6: 94 percent / pyridine / 8 h / Ambient temperature
7: 94 percent / Br2-HBr / pyridine; tetrahydrofuran / 2 h / Ambient temperature
8: 1.) t-BuOK; 2.) PPTS / 1.) DMSO, 40 deg C, 24 h; 2.) acetone/H2O, room temp., 24 h
9: 89 percent / 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
10: 85 percent / H2O2 (30percent), NaOH (4 M) / 2-methyl-propan-2-ol; tetrahydrofuran / 1 h / Ambient temperature
11: 90 percent / LDA / tetrahydrofuran / 0.5 h / 0 °C
12: 93 percent / tetrahydrofuran / 0.5 h / 0 deg C to room temp.
13: 92 percent / H2 / PtO2 / ethyl acetate / 12 h / Ambient temperature
14: 89 percent / 2,6-lutidine / CH2Cl2 / 0.08 h / 0 °C
15: 71 percent / 3,5-dimethylpyrazole/CrO3 / CH2Cl2 / 4 h / -20 - -10 °C
With
2,6-dimethylpyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; potassium tert-butylate; ammonia; hydrogen bromide; hydrogen; dihydrogen peroxide; bromine; pyridinium p-toluenesulfonate; lithium; toluene-4-sulfonic acid; orthoformic acid triethyl ester; pyridinium chlorochromate; lithium diisopropyl amide;
platinum(IV) oxide;
In
tetrahydrofuran; pyridine; dichloromethane; water; acetic anhydride; ethyl acetate; tert-butyl alcohol;
DOI:10.1016/S0040-4039(01)93715-3