Synthesis of Quinine

Structure of Quinine

C20H24N2O2

Principal investigatorMilan Uskokovic
Publication year1978
Synthesis typeTotal
Number of steps 14 (linear)
References
Helv. Chim. Acta 1973, 56, 1494. J. Am. Chem. Soc. 1978, 100, 571. J. Am. Chem. Soc. 1978, 100, 576.
Part 1 of 1
intermediate structure
  1. i-Pr2NLi
  2. MeOCO2Me
THF
-78 °C to RT, 4 h, 99%
intermediate structure
PtO2, HCl, H2
70 atm
H2O
60 °C, 82%
"The enantiomers were resolved with (-)-tartaric acid (29 % yield)."
intermediate structure
NCS
Et2O
RT, 60 min, 92%
intermediate structure
hν
CF3CO2H
0 °C, 50 min
See the Hofmann-Löffler-Freytag Reaction
intermediate structure
K2CO3, BzCl
H2O, PhH
RT, 2 h, 84% (2 steps)
See the Schotten-Baumann Reaction
intermediate structure
NaOH
H2O, MeOH
RT, 17 h, 99%
intermediate structure
KOt-Bu
DMSO, PhH
70 °C, 7 h, 88%
intermediate structure
CH2N2
Et2O, MeOH
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
MeOH, THF
RT, 20 min
intermediate structure
Ba(OH)2
H2O, MeOH
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
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