Synthesis of Nupharamine

Structure of Nupharamine

C15H25NO2

Principal investigatorSiegfried Blechert
Publication year2005
Synthesis typeTotal
Number of steps 9 (linear)
References
Synlett 2005, 2826.
Part 1 of 1
intermediate structure
0.015 atm
480 °C, 23%
"The yield was 46 % brsm."
intermediate structure
DEAD, Ph2PMe, Phthalimide
THF
0 °C to RT, 60 min, 50%
See the Mitsunobu Reaction
intermediate structure
CF3CO2H
CHCl3
0 °C to RT, 16 h
intermediate structure
MeNH2
EtOH
55 °C, 24 h
intermediate structure
Boc2O, NaHCO3
CHCl3, H2O
RT, 16 h, 81% (3 steps)
intermediate structure + intermediate structure
Grubbs-Hoveyda catalyst (2nd gen.)
CH2Cl2
40 °C, 72 h, 74%
See the Olefin Metathesis
intermediate structure
Pd/C, H2
Acetone
RT, 15 min, 1 atm
intermediate structure
CF3CO2H
CH2Cl2
RT, 60 min
intermediate structure
NaBH4
EtOH
0 °C, 60 min, 75% (3 steps)
intermediate structure
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