Synthesis of Morphine
C17H19NO3
Principal investigator | Marshall D. Gates |
---|---|
Publication year | 1952 |
Synthesis type | Total |
Number of steps | 27 (linear) |
References |
Part 1 of 1
Pyr,
BzCl
Dioxane
100 °C, 3 h, 71%
NaNO2
AcOH, H2O
0 °C, 2 h, 89%
Pd/C,
H2
1 atm
AcOH
RT, 45 min
FeCl3,
HCl
H2O
RT, 88% (2 steps)
SO2
H2O, MeOH
RT, 30 min, 91%
NaHSO3,
KOH
H2O, MeOH
RT, 80%
NaNO2
AcOH, H2O
-10 °C, 25 min, 97%
Pd/C,
H2SO4,
H2
1 atm
AcOH
RT, 60 min
FeCl3,
HCl
H2O
RT, 89% (2 steps)
KOH
H2O, MeOH
25-30 °C, 4 min, 97%
Cu2Cr2O5,
H2
27 atm
EtOH
124-131 °C, 4 h, 50%
NaH,
MeI
PhMe
Reflux, 3.5 h
LiAlH4
Et2O
Reflux, 48 h, 88% (2 steps)
"The enantiomers were resolved with dibenzoyl-(+)-tartaric acid (72 % yield)."
H2SO4
H2O
100 °C, 5 d, 28%
KOH,
NH2NH2
Diglyme
221-227 °C, 75 min, 33%
"The yield was 54 % brsm."
- Br2
- 2,4-Dinitrophenylhydrazine
AcOH
RT to reflux, 24 h, 41%
HCl
Acetone, H2O
Reflux, 20 min, 60%
PtO2,
H2
1 atm
EtOH
RT, 80%
- Br2 , NaOAc
- 2,4-Dinitrophenylhydrazine
AcOH
RT, 24 h, 26%
HCl
Acetone, H2O
Reflux, 20 min, 27%
LiAlH4
THF
Reflux, 46 h, 37%
Pyr.HCl
220 °C, 6 min, 34%