N-Benzyl-N-(Methoxymethyl)-N-Trimethylsilylmethylamine

Catalog Number	ACM93102057-4
CAS Number	93102-05-7
Structure
Molecular Weight	237.42 g/mol
Molecular Formula	C13H23NOSi
Boiling Point	78 °C(0.6 mmHg)
Purity	>98%
Appearance	Colorless to Light yellow clear liquid
Application	N-Benzyl-N-(Methoxymethyl)-N-Trimethylsilylmethylamine serves as a highly useful reagent in the synthesis of N-benzyl substituted pyrrolidines through [3+2] cycloaddition reactions with αβ-unsaturated esters This compound is particularly advantageous due to its ease of handling and effective in situ generation of N-benzyl azomethine ylide a key intermediate in these processes Utilizing trifluoroacetic acid or alternative catalysts such as LiF TBAF Me3SiOTf–CsF or Me3SiI–CsF the ylide reacts readily with electron-deficient alkenes to efficiently produce pyrrolidine derivatives and with alkynes to yield 3-pyrrolines which can subsequently be transformed into pyrroles The reagent supports stereospecific and concerted cycloadditions accommodating a variety of dipolarophiles including unsaturated esters ketones imides nitriles and sulfones Furthermore it enables the formation of fused bicyclic pyrrolidines and spirocyclic compounds offering a practical pathway for the large-scale synthesis of chiral pyrrolidines and 3-carboxy-1-azabicyclo[221]heptane derivatives a class of compounds with significant physiological activity
Storage	0-10 °CStore under inert gas
MDL Number	MFCD00674005
Reaxys Registry Number	4311216
Specific Gravity	0.93