Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigatorElias J. Corey
Publication year2006
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure + intermediate structure
Special reagent
RT, 30 h, 97%
intermediate structure
NH3
CF3CH2OH
40 °C, 5 h, 100%
intermediate structure
TMSOTf, Et3N
Pentane
0 °C to RT, 2 h
intermediate structure
I2
Et2O, THF
0 °C, 3 h, 84% (2 steps)
intermediate structure
Boc2O, Et3N, DMAP
CH2Cl2
RT, 4 h, 99%
intermediate structure
DBU
THF
Reflux, 12 h, 96%
intermediate structure
NBS, AIBN
CCl4
Reflux, 2 h, 95%
intermediate structure
Cs2CO3
EtOH
RT, 25 min, 100%
intermediate structure
N-Bromoacetamide, SnBr4
MeCN
-40 °C, 4 h, 75%
intermediate structure
n-Bu4N+ Br-, TMS2NK
DME
-20 °C, 10 min, 82%
intermediate structure
Cu(OTf)2, 3-Pentanol
0 °C, 12 h, 61%
intermediate structure
H3PO4
EtOH
intermediate structure