Synthesis of Physostigmine

Structure of Physostigmine

C15H21N3O2

Principal investigatorPercy L. Julian
Publication year1935
Synthesis typeTotal
Number of steps 10 (linear)
References
Part 1 of 1
intermediate structure
  1. Na
  2. Me2SO4
  3. EtOH , KOH , H2O
Xylene(s)
Reflux, 38 h, 96%
intermediate structure
Special reagent
PhH
Reflux, 30 min
intermediate structure
AlCl3
RT to 185 °C, , 92% (2 steps)
intermediate structure
Et2SO4, KOH
H2O
100 °C, 30 min, 68%
intermediate structure
ClCH2CN, NaOEt
EtOH
60 °C, 3 h, 84%
intermediate structure
H2SO4, PtO2, H2
1.5 atm
AcOH
RT, , 91%
intermediate structure
  1. PhCHO
  2. MeI
  3. HCl , H2O , EtOH
RT to 100 °C, 3 h, 91%
intermediate structure
Na
EtOH
RT, 2 h, 80%
intermediate structure
AlCl3
Petroleum ether
Reflux, ON, 91%
intermediate structure
  1. Na
  2. MeNCO
Et2O, PhH
RT, 60 min, 50%
intermediate structure