CAS 93102-05-7, Cat. No EN300-54483
Nonstabilized azomethine ylide precursor


N-(Methoxymethyl)-N-(trimethylsilylmethyl)-N-benzylamine is a convenient source of non-stabilized azomethine ylide that plays as a fascinating 1,3-dipole for a number of [3 + 2] or [3 + 3] cycloaddition reactions toward the construction of functionalized N-heterocycles[1], [2], [3], [4]. The intermediate forms in metal-free conditions in the presence of trifluoroacetic acid, zinc chloride, or cesium fluoride[5]. Reactive targets include classical ones such as aliphatic aldehydes, aryl isothiocyanates or activated four- and five-membered alkenes, but also medicinally appropriate C,N-cyclic azomethine imines, vinyl sulfonyl fluorides, cyanosulfones alkenyl boropinacolates[2].

Synonyms: N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine, N-benzyl-1-methoxy-N-((trimethylsilyl)methyl), methenamine benzyl(methoxymethyl)[(trimethylsilyl)methyl]amine, N-(methoxymethyl)-1-phenyl-N-(trimethylsilylmethyl)methenamine

Selected publication

  1. Synthesis of 6‐Azaspiro[4.3]Alkanes: Innovative Scaffolds for Drug Discovery.

    Chalyk B. A.; Isakov A. A.; Butko M. V.; Hrebeniuk K. V.; Savych O. V. et al. European J Org Chem 2017, 2017 (31), 4530–4542. DOI: 10.1002/ejoc.201700536

  2. Bicyclic Pyrrolidines for Medicinal Chemistry via [3+2]-Cycloaddition.

    Savych V. I.; Mykhalchuk V. L.; Melnychuk P. V.; Isakov A. O.; Savchuk T. et al. J Org Chem 2021, 86 (19), 13289–13309. DOI: 10.1021/acs.joc.1c01327

  3. [3+2] Cycloaddition of Alkynyl Boronates and in Situ Generated Azomethine Ylide.

    Liashuk O. S.; Ryzhov I. A.; Hryshchuk, O V.; Volovenko Y. M.; Grygorenko O. O. Chemistry – A European Journal 2024. DOI: 10.1002/chem.202303504

  4. Synthesis of 3‐Borylated Pyrrolidines by 1,3‐Dipolar Cycloaddition of Alkenyl Boronates and Azomethine Ylide.

    Liashuk O. S.; Ryzhov I. A.; Hryshchuk O. V.; Vashchenko B. V. et al. Chemistry – A European Journal 2022, 28 (54). DOI: 10.1002/chem.202202117

  5. N-Benzyl-N-(Methoxymethyl)-N-Trimethylsilylmethylamine.

    Orlek B. S. Encyclopedia of Reagents for Organic Synthesis 2001. DOI: 10.1002/047084289X.rb064