Synthesis of Quinine

Structure of Quinine

C20H24N2O2

Principal investigatorMilan Uskokovic
Publication year1978
Synthesis typeTotal
Number of steps 14 (linear)
References
Part 1 of 1
intermediate structure
  1. i-Pr2NLi
  2. MeOCO2Me
THF
-78 °C to RT, 4 h, 99%
intermediate structure
H2, PtO2, HCl
H2O
60 °C, , 82%
"The enantiomers were resolved with (-)-tartaric acid (29 % yield)."
intermediate structure
NCS
Et2O
RT, 60 min, 92%
intermediate structure
CF3CO2H
0 °C, 50 min
intermediate structure
BzCl, K2CO3
PhH, H2O
RT, 2 h, 84% (2 steps)
intermediate structure
NaOH
MeOH, H2O
RT, 17 h, 99%
intermediate structure
KOt-Bu
PhH, DMSO
70 °C, 7 h, 88%
intermediate structure
CH2N2
MeOH, Et2O
RT, 90 min, 92%
intermediate structure + intermediate structure
i-Pr2NLi
THF
-78 °C to RT, 60 min, 78%
intermediate structure
H2SO4
H2O
Reflux, 24 h, 75%
intermediate structure
i-Pr2NCl, H3PO4
RT, 24 h
intermediate structure
NaBH4
THF, MeOH
RT, 20 min
intermediate structure
Ba(OH)2
MeOH, H2O
RT, 18 h, 27% (3 steps)
intermediate structure
i-Bu2AlH
PhMe
-78 °C, , 33%
"Quinine was selectively cristallized (as a tartrate salt) from the resulting two diastereoisomers."
intermediate structure