93102-05-7

50-00-0

53215-95-5

93102-05-7

N-[(Trimethylsilyl)methyl]benzylamine (Intermediate P15, 28.588 g, 144.89 mmol) was added dropwise to the formaldehyde solution (37%, 16.816 g, 207.19 mmol) at 0 °C. Subsequently, solid potassium carbonate (16.182 g, 115.91 mmol) was added to the reaction mixture and stirred continuously for 2 hours at room temperature. After completion of the reaction, water (50 mL) was added for dilution and the mixture was extracted with ether (2 x 50 mL). The organic layer was subsequently washed with brine and dried with anhydrous sodium sulfate. Finally, the solvent and desiccant were removed by reduced pressure distillation to afford 33.551 g of the yellow oily target product N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine in 97.5% yield. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.35-7.18 (m, 5H), 3.99 (s, 2H), 3.75 (s, 2H), 3.22 (s, 3H), 2.18 (s, 2H), 0.13 (s, 9H).

Useful reagent in synthesizing N-benzyl substituted pyrrolidines by [3+2] cycloaddition to α,ßunsaturated esters.

N-Methoxymethyl-N-(trimethylsilylmethyl)benzylamine is most conveniently prepared by treatment of benzylamine with chloromethyltrimethylsilane followed by formaldehyde and methanol. Access to higher ether homologs is achieved by replacing methanol with the appropriate alcohol. An alternate procedure involves alkylation of lithium N-benzyltrimethylsilymethylamide with methoxymethyl chloride.