SCALABLE AND GREEN PROCESS FOR THE SYNTHESIS OF ANTICANCER DRUG LENALIDOMIDE

Authors

  • Yuri Ponomaryov Latvian Institute of Organic Synthesis
  • Valeria Krasikova Latvian Institute of Organic Synthesis
  • Anton Lebedev Latvian Institute of Organic Synthesis
  • Dmitri Chernyak Latvian Institute of Organic Synthesis
  • Larisa Varacheva Latvian Institute of Organic Synthesis
  • Alexandr Chernobroviy Latvian Institute of Organic Synthesis

DOI:

https://doi.org/10.1007/1944

Keywords:

lenalidomide, thalidomide, multiple myeloma, bromination, reduction

Abstract

A new process for the synthesis of anticancer drug lenalidomide was developed, using platinum group metal-free and efficient reduction of nitro group with the iron powder and ammonium chloride. It was found that the bromination of the key raw material, methyl 2-methyl-3-nitrobenzoate, could be carried out in chlorine-free solvent methyl acetate without forming significant amounts of hazardous by-products. We also have compared the known synthetic methods for cyclization of methyl 2-(bromomethyl)-3-nitrobenzoate and 3-aminopiperidinedione to form lenalidomide nitro precursor.

How to Cite
Ponomaryov, Y.; Krasikova, V.; Lebedev, A.; Chernyak, D.; Varacheva, L.; Chernobroviy, A. Chem. Heterocycl. Compd. 2015, 51, 133. [Khim. Geterotsikl. Soedin. 2015, 51, 133.]

For this article in the English edition see DOI 10.1007/s10593-015-1670-0

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Published

2015-03-13

Issue

Vol. 51 No. 2 (2015)

Section

Original Papers