Synthesis of Morphine

Structure of Morphine

C17H19NO3

Principal investigatorCatherine Guillou
Publication year2008
Synthesis typeFormal
Number of steps 18 (linear)
References
Chem. Eur. J. 2008, 14, 6606.
Part 1 of 1
intermediate structure
Li
NH3, t-BuOH
-78 °C, 6 h, 97%
See the Birch Reduction
intermediate structure
(CH2OH)2, BF3.OEt2
Et2O
0 °C, 60 min, 81%
intermediate structure + intermediate structure
DMAP, EDC
CH2Cl2
0 °C to RT, 5 h, 80%
intermediate structure
Et3N, Pd2(dba)3
DMF
140 °C, 5 h, 60%
See the Mizoroki-Heck Reaction
intermediate structure
Ph3C+ BF4-
CH2Cl2
RT, 2 h, 92%
intermediate structure
(PhSeO)2O
PhCl
120 °C, 8 h, 60%
intermediate structure
BnNHMe
RT, 16 h
See the Michael Addition
intermediate structure
LiAlH4
THF
0 °C to Reflux, 2 h, 77% (2 steps)
intermediate structure
CH(OMe)2NMe2
Decalin
250 °C, 2 h, 44%
See the Eschenmoser-Claisen Rearrangement
intermediate structure
Ti(Oi-Pr)4, PhSiH3
RT, 35 min
intermediate structure
TsOH
PhMe
RT, 16 h, 55% (2 steps)
See the Friedel-Crafts Alkylation
intermediate structure
ClCO2CH(Cl)CH3
DCE
0 °C to Reflux, 70 min
intermediate structure
Et3N, TsCl
CH2Cl2
RT, 16 h, 83% (2 steps)
intermediate structure
SeO2
Dioxane , t-BuOH
50 °C, 30 h
intermediate structure
Dess-Martin Periodinane
CH2Cl2
RT, 2 h
See the Dess-Martin Oxidation
intermediate structure
NaBH4
MeOH
0 °C to RT, 60 min, 28% (3 steps)
intermediate structure
Li
NH3, t-BuOH, THF
-78 °C, 8 min, 51%
"The yield was 62 % brsm."
intermediate structure
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Remaining...
91% (1 step)
"See : J. Med. Chem. 1977, 20, 164."
intermediate structure