Synthesis of Morphine

C17H19NO3
Principal investigator | James D. White |
---|---|
Publication year | 1999 |
Synthesis type | Formal |
Number of steps | 28 (linear) |
References |
Part 1 of 1
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[RhCl(COD)]2,
H2
1 atm
MeOH, THF
RT, 10 h, 100%

Br2
AcOH
RT, 10 min, 92%


Pd(OH)2,
NaHCO3,
H2
1 atm
MeOH
RT, 45 min, 99%

LiOH
H2O, THF
RT, 12 h, 100%





CH2N2
Et2O, EtOAc
RT, 90%

NaHCO3,
Br2
CHCl3
0 °C, 90 min, 70%

DBU
PhH
68 °C, 4 h, 90%

NaBH4
CH2Cl2, i-PrOH
RT, 12 h, 99%

Pd/C,
NaHCO3,
H2
1 atm
MeOH
RT, 24 h, 75%

CH2(OMe)2,
P2O5
CHCl3
RT, 4 h, 86%

LiOH
H2O, THF
RT, 20 h, 100%

CH2N2,
(COCl)2
Et2O, PhH
RT, 19 h, 63%

Rh2(CH3CONH)4
CH2Cl2
RT, 60 min, 65%

NH2OH.HCl,
NaOAc
MeOH
RT, 6 h, 90%

DMAP,
Et3N,
BsCl
CH2Cl2
RT, 60 min


NaH,
MeI
PhH
Reflux, 5 h, 95%

HBr
H2O, MeCN
RT, 2 h, 95%


PhSeCl,
KOt-Bu
t-BuOH, THF
0 °C to RT, 90 min

NaIO4
H2O, THF
RT, 30 h, 64% (2 steps)

LiAlH4
THF
Reflux, 6 h, 70%

Remaining...
91% (1 step)
"See : J. Med. Chem. 1977, 20, 164."
