Multi-step reaction with 15 steps
1: 94 percent / 2 N H2SO4 / tetrahydrofuran / 48 h / 60 °C
2: 65 percent / camphorsulfonic acid (CSA) / tetrahydrofuran / 1.) rt, 20 h, 2.) 60 deg C, 6 h
3: 99 percent / DMAP, pyridine / CH2Cl2 / 0.33 h
4: camphorsulfonic acid (CSA) / benzene / 27 h / Heating
5: 75 percent / Hg(CN)2, 4A molecular sieves / benzene / 1 h / Ambient temperature
6: 73 percent / 10percent Pd/C / methanol / 4 h / Heating
7: K2CO3 / methanol; tetrahydrofuran / 23 h / Ambient temperature
8: DMAP, Et3N / dimethylformamide / 12 h / Ambient temperature
9: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 2.) from -78 deg C to rt
10: 88 percent / H2 / 10percent Pd/C / ethyl acetate / Ambient temperature
11: 96 percent / 4-pyrrolidinopyridine, Et3N / 4.5 h / Ambient temperature
12: 100 percent / Et3N / methanol / 23 h / Ambient temperature
13: Ph3P (TPP), diisopropyl azodicarboxylate (DIAD) / tetrahydrofuran / 27 h / Ambient temperature
14: 83 percent / NaBH4 / methanol; tetrahydrofuran / 0.08 h / -20 °C
15: 91 percent / 4-pyrrolidinopyridine, pyridine, Et3N / 20 h / Ambient temperature
With
pyridine; dmap; sodium tetrahydroborate; di-isopropyl azodicarboxylate; 4 A molecular sieve; sulfuric acid; camphor-10-sulfonic acid; hydrogen; mercury(II) cyanide; potassium carbonate; 4-pyrrolidin-1-ylpyridine; ozone; triethylamine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;