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Oseltamivir
"Kilogram quantities of drug substance have been prepared by this route in standard pilot plant equipment."
C16H28N2O4
| Author | John C. Rohloff |
|---|---|
| Publication year | 1998 |
| Synthesis type | Total synthesis |
| Number of steps | 12 (linear) |
| Reference |
Browse hundreds of other total syntheses.
Part 1 of 1
2,2-Dimethoxypropane, TsOH
Acetone
Reflux, 2 h
Reflux, 2 h
NaOEt
EtOH
RT, 2 h
RT, 2 h
MsCl, Et3N
CH2Cl2
0-5 °C, 90 min, 69 % (3 steps)
0-5 °C, 90 min, 69 % (3 steps)
SO2Cl2, Pyr
CH2Cl2
-30 to -20 °C, 3.5 h, 44 %
-30 to -20 °C, 3.5 h, 44 %
3-Pentanone, HClO4
H2O
40 °C, 4-20 h, 95 %
40 °C, 4-20 h, 95 %
BH3.Me2S, TMSOTf
CH2Cl2
-20 to -10 °C, 42 min
-20 to -10 °C, 42 min
KHCO3
EtOH, H2O
55 to 65 °C, 60 min, 64 % (2 steps)
55 to 65 °C, 60 min, 64 % (2 steps)
NaN3, NH4Cl
EtOH, H2O
70-75 °C, 12-18 h, 86 %
Selectivity : 91:09
70-75 °C, 12-18 h, 86 %
Selectivity : 91:09
+ 
Me3P
MeCN
RT to 38 °C, 2 h
RT to 38 °C, 2 h
NaN3, NH4Cl
DMF
70 to 80 °C, 12-18 h
70 to 80 °C, 12-18 h
H2, Ni (Raney)
1 atm
EtOH
RT, 10-16 h, 71 %
1 atm
RT, 10-16 h, 71 %
