Multi-step reaction with 7 steps
1: 86.8 percent / hydrogen / 10percent Pd/C / ethyl acetate / 20 h / 2585.7 Torr / Ambient temperature
2: 1N HCl / Heating
3: 62.9 percent / pyridine / CHCl3 / 72 h / Ambient temperature
4: 1) ClCOOEt, Et3N, 2) NaN3 / 1) acetone, H2O, 2 min, 0 to 5 deg C, 2) acetone, H2O, 4 min, 0 to 5 deg C
5: 84.2 percent / toluene / 20 h / Heating
6: 1) Hg(OAc)2, 2) H2S / 1) EtOH, 15 min, RT, 2) CH2Cl2, 0, to 5 deg C, 1 h
7: 1) diphenylchlorophosphate, (i-Pr)2NH / 1) CH3CN, 0 to 5 deg C, 1 h, 2) CH3CN, RT, 6 d
With
pyridine; hydrogenchloride; sodium azide; hydrogen sulfide; mercury(II) diacetate; hydrogen; chloroformic acid ethyl ester; triethylamine; diisopropylamine; chlorophosphoric acid diphenyl ester;
palladium on activated charcoal;
In
chloroform; ethyl acetate; toluene;