Development of the synthetic route to 5-hydroxymethyl tolterodine, a key synthetic intermediate of Toviaz, via an organic solvent-free Rh-catalyzed asymmetric 1,4-addition

Aki Hirasawa; Hiroki Shibata; Gaku Okamoto; Toshihide Takemoto; Takeaki Katayama; Toshiyuki Oshiki; Toshinobu Korenaga

doi:10.1039/D5OB01887K

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Development of the synthetic route to 5-hydroxymethyl tolterodine, a key synthetic intermediate of Toviaz, via an organic solvent-free Rh-catalyzed asymmetric 1,4-addition

Aki Hirasawa,^a Hiroki Shibata,^a Gaku Okamoto,^a Toshihide Takemoto,^b Takeaki Katayama,^b Toshiyuki Oshiki^c and Toshinobu Korenaga

*^a

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* Corresponding authors

^a Department of Science and Engineering, Faculty of Science and Engineering, Iwate University, 4-3-5 Ueda, Morioka, Iwate 020-8551, Japan
E-mail: korenaga@iwate-u.ac.jp

^b Central Research Laboratory, Technology and Development Division, Kanto Chemical Co., Inc., Soka, Saitama 340-0003, Japan

^c Department of Applied Chemistry, Okayama University, 3-1-1 Tsushimanaka, Okayama, Japan

Abstract

A synthetic route to Toviaz (fesoterodine fumarate) and its key intermediate 5-hydroxymethyl tolterodine (5-HMT) was markedly improved by employing an organic solvent-free rhodium-catalyzed asymmetric 1,4-addition. Under these conditions, the reactivity depended strongly on the substrates’ melting points, even though the reaction temperature was more than 20 °C below them.

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DOI: https://doi.org/10.1039/D5OB01887K
Article type: Communication
Submitted: 02 Dec 2025
Accepted: 07 Feb 2026
First published: 12 Feb 2026

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Org. Biomol. Chem., 2026, Advance Article

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Development of the synthetic route to 5-hydroxymethyl tolterodine, a key synthetic intermediate of Toviaz, via an organic solvent-free Rh-catalyzed asymmetric 1,4-addition

A. Hirasawa, H. Shibata, G. Okamoto, T. Takemoto, T. Katayama, T. Oshiki and T. Korenaga, Org. Biomol. Chem., 2026, Advance Article , DOI: 10.1039/D5OB01887K

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Organic & Biomolecular Chemistry

Development of the synthetic route to 5-hydroxymethyl tolterodine, a key synthetic intermediate of Toviaz, via an organic solvent-free Rh-catalyzed asymmetric 1,4-addition

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Development of the synthetic route to 5-hydroxymethyl tolterodine, a key synthetic intermediate of Toviaz, via an organic solvent-free Rh-catalyzed asymmetric 1,4-addition

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