Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigatorJohn C. Rohloff
Publication year1998
Synthesis typeTotal
Number of steps 12 (linear)
References
Part 1 of 1
intermediate structure
2,2-Dimethoxypropane, TsOH
Acetone
Reflux, 2 h
intermediate structure
NaOEt
EtOH
RT, 2 h
intermediate structure
MsCl, Et3N
CH2Cl2
0-5 °C, 90 min, 69% (3 steps)
intermediate structure
SO2Cl2, Pyr
CH2Cl2
-30 to -20 °C, 3.5 h, 44%
intermediate structure
3-Pentanone, HClO4
H2O
40 °C, 4-20 h, 95%
intermediate structure
BH3.Me2S, TMSOTf
CH2Cl2
-20 to -10 °C, 42 min
intermediate structure
KHCO3
EtOH, H2O
55 to 65 °C, 60 min, 64% (2 steps)
intermediate structure
NaN3, NH4Cl
EtOH, H2O
70-75 °C, 12-18 h, 86%
intermediate structure + intermediate structure
Me3P
MeCN
RT to 38 °C, 2 h
intermediate structure
NaN3, NH4Cl
DMF
70 to 80 °C, 12-18 h
intermediate structure
Ac2O, NaHCO3
CH2Cl2, Hexane(s), H2O
RT, 60 min, 43% (3 steps)
intermediate structure
H2, Ni (Raney)
EtOH
RT, 10-16 h, 71%
intermediate structure