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Named reactions

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Search synthesis

Morphine

Chemical structure of Morphine
C17H19NO3
Author Marshall D. Gates
Publication year 1952
Synthesis type Total synthesis
Number of steps 27 (linear)
References

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
BzCl, Pyr
Dioxane
100 °C, 3 h, 71 %
Chemical structure
NaNO2
AcOH, H2O
0 °C, 2 h, 89 %
Chemical structure
H2, Pd/C
1 atm
AcOH
RT, 45 min
Chemical structure
FeCl3, HCl
H2O
RT, 88 % (2 steps)
Chemical structure
SO2
MeOH, H2O
RT, 30 min, 91 %
Chemical structure
Me2SO4, K2CO3, NaHSO3
Acetone
RT, 3 h, 82-86 %

See the Williamson Ether Synthesis
Chemical structure
KOH, NaHSO3
MeOH, H2O
RT, 80 %
Chemical structure
NaNO2
AcOH, H2O
-10 °C, 25 min, 97 %
Chemical structure
H2, Pd/C, H2SO4
1 atm
AcOH
RT, 60 min
Chemical structure
FeCl3, HCl
H2O
RT, 89 % (2 steps)
Chemical structure
NCCH2CO2Et, K3Fe(CN)6, Et3N
EtOH, H2O
RT, 11 min, 84 %

See the Michael Addition
Chemical structure
KOH
MeOH, H2O
25-30 °C, 4 min, 97 %
Chemical structure
1,3-Butadiene
Dioxane
85-87 °C, 72 h, 66 %

See the Diels-Alder Reaction
Chemical structure
H2, Cu2Cr2O5
27 atm
EtOH
124-131 °C, 4 h, 50 %
Chemical structure
NH2NH2, KOH
Diethylene glycol
155 °C, 60 min, 92 %

See the Wolff-Kishner Reduction
Chemical structure
NaH, MeI
PhMe
Reflux, 3.5 h
Chemical structure
LiAlH4
Et2O
Reflux, 48 h, 88 % (2 steps)

The enantiomers were resolved with dibenzoyl-(+)-tartaric acid (72 % yield).
Chemical structure
H2SO4
H2O
100 °C, 5 d, 28 %
Chemical structure
NH2NH2, KOH
Diglyme
221-227 °C, 75 min, 33 %

The yield was 54 % brsm.
Chemical structure
Ph2CO, KOt-Bu
t-BuOH, PhH
Reflux, 2.5 h, 90 %

See the Oppenauer Oxidation
Chemical structure
Br2, 2,4-Dinitrophenylhydrazine
AcOH
RT to reflux, 24 h, 41 %
Chemical structure
HCl
Acetone, H2O
Reflux, 20 min, 60 %
Chemical structure
H2, PtO2
1 atm
EtOH
RT, 80 %
Chemical structure
Br2, NaOAc, 2,4-Dinitrophenylhydrazine
AcOH
RT, 24 h, 26 %
Chemical structure
HCl
Acetone, H2O
Reflux, 20 min, 27 %
Chemical structure
LiAlH4
THF
Reflux, 46 h, 37 %
Chemical structure
Pyr.HCl
220 °C, 6 min, 34 %
Chemical structure

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