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Morphine
C17H19NO3
| Author | James D. White |
|---|---|
| Publication year | 1999 |
| Synthesis type | Formal synthesis |
| Number of steps | 28 (linear) |
| Reference |
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Part 1 of 1
+ 
H2, [RhCl(COD)]2
1 atm
RT, 10 h, 100 %
Selectivity : 97:03 er
Br2
AcOH
RT, 10 min, 92 %
RT, 10 min, 92 %
H2, Pd(OH)2, NaHCO3
1 atm
MeOH
RT, 45 min, 99 %
1 atm
RT, 45 min, 99 %
LiOH
THF, H2O
RT, 12 h, 100 %
RT, 12 h, 100 %
+ 
CH2N2
EtOAc, Et2O
RT, 90 %
RT, 90 %
Br2, NaHCO3
CHCl3
0 °C, 90 min, 70 %
0 °C, 90 min, 70 %
DBU
PhH
68 °C, 4 h, 90 %
68 °C, 4 h, 90 %
NaBH4
CH2Cl2, i-PrOH
RT, 12 h, 99 %
RT, 12 h, 99 %
H2, Pd/C, NaHCO3
1 atm
MeOH
RT, 24 h, 75 %
1 atm
RT, 24 h, 75 %
CH2(OMe)2, P2O5
CHCl3
RT, 4 h, 86 %
RT, 4 h, 86 %
LiOH
THF, H2O
RT, 20 h, 100 %
RT, 20 h, 100 %
(COCl)2, CH2N2
PhH, Et2O
RT, 19 h, 63 %
RT, 19 h, 63 %
Rh2(CH3CONH)4
CH2Cl2
RT, 60 min, 65 %
RT, 60 min, 65 %
NH2OH.HCl, NaOAc
MeOH
RT, 6 h, 90 %
RT, 6 h, 90 %
BsCl, Et3N, DMAP
CH2Cl2
RT, 60 min
RT, 60 min
NaH, MeI
PhH
Reflux, 5 h, 95 %
Reflux, 5 h, 95 %
HBr
MeCN, H2O
RT, 2 h, 95 %
RT, 2 h, 95 %
KOt-Bu, PhSeCl
THF, t-BuOH
0 °C to RT, 90 min
0 °C to RT, 90 min
NaIO4
THF, H2O
RT, 30 h, 64 % (2 steps)
RT, 30 h, 64 % (2 steps)
LiAlH4
THF
Reflux, 6 h, 70 %
Reflux, 6 h, 70 %
Remaining...
See : J. Med. Chem. 1977, 20, 164.
