A New Bicyclic Pyrrolidine Block for Nirmatrelvir and Analogues

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Abstract

To study the chemical properties and potential use in the synthesis of Nirmatrelvir and related compounds, a key block, ((1R,5S))-2-ethoxy-6,6-dimethyl-3-azabicyclo[3.1.0]hex-2-ene, which is readily available from (+)-3-carene and obtained by "enol-ethylation" of ((1R,5S))-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2-one with triethyloxonium tetrafluoroborate ((Et3O)+BF4 ), was proposed.

About the authors

G. R Sunagatullina

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Email: gsunagatullina95@mail.ru
Ufa, Russia

G. A Shavaleeva

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Ufa, Russia

Z. R Valiullina

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Ufa, Russia

M. S Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Ufa, Russia

References

  1. Lamb Y.N. Drugs, 2022, 82, 585–591. https://doi.org/10.1007/s40265-022-01692-5
  2. Njoroge F.G., Chen K.X., Shih N.-Y., Piwinski J.J. Accounts Chem. Res., 2008, 41, 50–59. https://doi.org/10.1021/ar700109k
  3. Dayan Elshan N.G.R., Wolff K.C., Riva L., Woods A.K., Grabovyi G., Wilson K., Pedroarena J., Ghorai S., Nazarian A., Weiss F., Liu Y., Mazumdar W., Song L., Okwor N., Malvin J., Bakowski M.A., Beutler N., Kirkpatrick M.G., GebaraLamb A., Huang E., Nguyen-Tran V.T.B., Chi V., Li S., Rogers T.F., McNamara C.W., Gupta A.K., Rahimi A., Chen J.J., Joseph S.B., Schultz P.G., Chatterjee A.K. J. Med. Chem., 2024, 67, 2369–2378. https://doi.org/10.1021/acs.jmedchem.3c01938
  4. Preschel H.D., Otte R.T., Zhuo Y., Ruscoe R.E., Burke A.J., Kellerhals R., Horst B., Hennig S., Janssen E., Green A.P., Turner N.J., Ruijter E. J. Org. Chem., 2023, 88, 12565–12571. https://doi.org/10.1021/acs.joc.3c01274
  5. European Patent 0149289; Chem. Abstracts, 1984, 101, 38671m.
  6. Huang P.Q. Tetrahedron Lett., 2001, 42, 9039–9041.
  7. Verkade J.M.M., van Hemert L.J.C., Quaedflieg P.J.L.M. Tetrahedron Lett., 2006, 47, 8109–8113. https://doi.org/10.1016/j.tetlet.2006.09.044

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