Synthesis of Morphine
C17H19NO3
Principal investigator | Kenner C. Rice |
---|---|
Publication year | 1980 |
Synthesis type | Total |
Number of steps | 18 (linear) |
References |
Part 1 of 1
+
200 °C, 2 h, 95%
NaBH3CN
H2O, MeOH
Reflux, 90 min, 86% (2 steps)
HCO2Ph
EtOAc
Reflux, 45 min, 94%
(CH2OH)2,
MsOH
THF
RT, 60 min
N-Bromoacetamide
THF
0-5 °C, 30 min
HCO2H
H2O
RT, 60 min, 90% (3 steps)
HF,
TfOH,
NH4F
H2O
0 °C, 72-96 h, 60%
HCl
H2O, MeOH
Reflux, 18 h, 98%
Br2
AcOH
RT, 2 h
NaOH
CHCl3, H2O
0 °C
CH2O,
H2,
NaOAc,
Pd/C
AcOH, H2O
79% (3 steps)
ClCO2Me
PhH
Reflux, 16 h, 100%
HCl,
PhSeCl
EtOAc, H2O
RT, 4.5 h, 85%
NaIO4
EtOAc, H2O
RT, 20 h, 68%
LiAlH4
THF
Reflux, 71%
BBr3
CHCl3
RT, 17 min, 91%