Synthesis of Morphine

Structure of Morphine

C17H19NO3

Principal investigatorKathlyn A. Parker
Publication year1992
Synthesis typeFormal
Number of steps 13 (linear)
References
J. Am. Chem. Soc. 1992, 114, 9689.
Part 1 of 1
intermediate structure
Li
NH3, t-BuOH
-68 °C, 3 h, 97%
See the Birch Reduction
intermediate structure
  1. TsCl , Et3N
  2. HCl , H2O
THF
RT, 9 h, 81%
intermediate structure
K2CO3, MeI
Acetone
RT, 24 h, 96%
intermediate structure
NaBH4, CeCl3
MeOH
0 °C, 30 min, 97%
See the Luche Reduction
intermediate structure
mCPBA
CH2Cl2
0 °C, 2 h, 92%
See the Prilezhaev Reaction
intermediate structure
Ti(Oi-Pr)4
PhH
Reflux, 2 h, 85%
intermediate structure
TBSOTf, i-Pr2NEt
-78 °C, 10 min, 82%
intermediate structure + intermediate structure
n-Bu3P, DEAD
THF
0 °C, 4 h, 83%
See the Mitsunobu Reaction
intermediate structure
HF
H2O, MeCN
RT, 24 h, 98%
intermediate structure
AIBN, n-Bu3SnH
PhH
130 °C, 35 h, 35%
intermediate structure
Li, NH3
t-BuOH, THF
-78 °C, 10 min, 85%
intermediate structure
(COCl)2, Et3N
DMSO
-78 °C to RT, 2.5 h, 83%
See the Swern Oxidation
intermediate structure
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Remaining...
37% (5 steps)
"See : Heterocycles 1977, 6, 1157; J. Med. Chem. 1977, 20, 164."
intermediate structure