Synthesis of Morphine
C17H19NO3
Principal investigator | Catherine Guillou |
---|---|
Publication year | 2008 |
Synthesis type | Formal |
Number of steps | 18 (linear) |
References |
Part 1 of 1
+
(CH2OH)2,
BF3.OEt2
Et2O
0 °C, 60 min, 81%
DMAP,
EDC
CH2Cl2
0 °C to RT, 5 h, 80%
Ph3C+ BF4-
CH2Cl2
RT, 2 h, 92%
(PhSeO)2O
PhCl
120 °C, 8 h, 60%
LiAlH4
THF
0 °C to Reflux, 2 h, 77% (2 steps)
Ti(Oi-Pr)4,
PhSiH3
RT, 35 min
ClCO2CH(Cl)CH3
DCE
0 °C to Reflux, 70 min
Et3N,
TsCl
CH2Cl2
RT, 16 h, 83% (2 steps)
SeO2
Dioxane , t-BuOH
50 °C, 30 h
NaBH4
MeOH
0 °C to RT, 60 min, 28% (3 steps)
Li
NH3, t-BuOH, THF
-78 °C, 8 min, 51%
"The yield was 62 % brsm."
Remaining...
91% (1 step)
"See : J. Med. Chem. 1977, 20, 164."