Synthesis of Oseltamivir

Structure of Oseltamivir

C16H28N2O4

Principal investigator	John C. Rohloff
Publication year	1998
Synthesis type	Total
Number of steps	12 (linear)
References	J. Org. Chem. 1998, 63, 4545.

Part 1 of 1

intermediate structure

TsOH, 2,2-Dimethoxypropane

Acetone

Reflux, 2 h

intermediate structure

NaOEt

EtOH

RT, 2 h

intermediate structure

Et3N, MsCl

CH2Cl2

0-5 °C, 90 min, 69% (3 steps)

intermediate structure

Pyr, SO2Cl2

CH2Cl2

-30 to -20 °C, 3.5 h, 44%

intermediate structure

HClO4, 3-Pentanone

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, H2O, Hexane(s)

RT, 60 min, 43% (3 steps)

See the Schotten-Baumann Reaction

intermediate structure

H2, Ni (Raney)

1 atm

EtOH

RT, 10-16 h, 71%

intermediate structure

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