Multi-step reaction with 12 steps
1: 86 percent / piperidine / pyridine / 1.) 105 deg C, 3 h, 2.) 145 deg C, 1 h
2: 88 percent / H2 / 10percent Pd-C / methanol / 12 h / Ambient temperature
3: 89 percent / K2CO3 / acetone / 20 h / Heating
4: 96 percent / aq. KOH / methanol; tetrahydrofuran / 2 h / Ambient temperature
5: Et3N / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) room temp., 50 min
6: n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) -78 deg C, 15 min and room temp., 4 h
7: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 min
8: 30percent H2O2, LiOH / tetrahydrofuran; H2O / 1.5 h / 0 °C
9: p-TsOH / 8 h / Heating
10: 85 percent / H2 / 10percent Pd-C / tetrahydrofuran / 8 h / 760 Torr / Ambient temperature
11: 82 percent / EDC, HOBT / tetrahydrofuran; dimethylformamide / 20 h / 0 °C
With
piperidine; potassium hydroxide; lithium hydroxide; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00088a009