CAS 93102-05-7: N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine

S00978 - N-Benzyl-N-(methoxymethyl)-N-(trimethylsilylmethyl)-amine (tech)

N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine is a chiral, electron deficient reagent that reacts with aldehydes and boronic esters to form products with high chemical yields. This compound can be used as a catalyst for acylation reactions, such as the synthesis of p-nitrophenol. N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine is synthesized by the reaction of trifluoroacetic acid and an amine, followed by chloroformate displacement. The product is then reacted with acylating agents in the presence of catalysts.

N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine forms azomethine ylides which readily undergo [3+2] cycloaddition to α,β-unsaturated esters affording N-benzyl substituted pyrrolidines in good yields. It reacts with asymmetric 1,3-dipolar cycloadditions in the practical, large-scale synthesis of chiral pyrrolidines. It is used in the the synthesis of 3-carboxy-1-azabicyclo[2.2.1]heptane derivatives, an important class of physiologically active compounds. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications N-(Methoxymethyl)-N-[(trimethylsilyl)methyl]benzenemethanamine is used in the synthesis of pyrrolidine derivatives as novel sodium channel blockers used to treat ischemic related ailments. References Seki, M. et al.: Bioorg. Med. Chem. Lett., 23, 4230 (2013);

N-Benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methylamine

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.