154344-51-1

Basic information

• Product Name: Pyrrolidine, 1-(phenylmethyl)-2,5-bis(trimethylsilyl)-
• Synonyms: Pyrrolidine,1-(phenylmethyl)-2,5-bis(trimethylsilyl);2,5-bis(trimethylsilyl)-N-benzylpyrrolidine
• CAS NO: 154344-51-1
• Molecular Formula: C17H31NSi2
• Molecular Weight: 305.611
• Mol File: 154344-51-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 336.8±42.0 °C(Predicted)
• Density: 0.92±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Pyrrolidine, 1-(phenylmethyl)-2,5-bis(trimethylsilyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolidine, 1-(phenylmethyl)-2,5-bis(trimethylsilyl)-(154344-51-1)
• EPA Substance Registry System: Pyrrolidine, 1-(phenylmethyl)-2,5-bis(trimethylsilyl)-(154344-51-1)

Safety Data

• Hazardous Substances Data: 154344-51-1(Hazardous Substances Data)

Usage

General Description

Pyrrolidine, 1-(phenylmethyl)-2,5-bis(trimethylsilyl)- is a chemical compound with the molecular formula C17H31NSi2. It is a substituted pyrrolidine derivative with a phenylmethyl group and two trimethylsilyl groups attached to the nitrogen atom. Pyrrolidine, 1-(phenylmethyl)-2,5-bis(trimethylsilyl)- is commonly used as a reagent in organic synthesis and can act as a chiral auxiliary in asymmetric synthesis. It has also been utilized in the development of pharmaceuticals and agrochemicals due to its versatile reactivity and potential pharmacological properties. Additionally, it is important to handle this compound with care and in accordance with proper safety precautions due to its potential hazards.

Upstream product

• 100-39-0 benzyl bromide 
• 178618-16-1 2,5-bis(trimethylsilyl)pyrrolidine 
• 159153-38-5 N-Boc-2,5-bis(trimethylsilyl)pyrrolidine 
• 137496-67-4 N-tert-butoxycarbonyl-2-trimethylsilylpyrrolidine 
• 100-44-7 benzyl chloride 
• 75-77-4 chloro-trimethyl-silane 
• 86953-79-9 tert-butyl pyrrolidine-1-carboxylate 

Downstream Products

• 201293-24-5 7-Benzyl-7-aza-bicyclo[2.2.1]hept-2-ene-2-carboxylic acid ethyl ester 
• 446873-09-2 [(1R,2R,3S,4S)-7-Benzyl-3-(6-chloro-pyridin-3-yl)-7-aza-bicyclo[2.2.1]hept-2-yl]-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone 
• 446872-99-7 ((1R,2S,4S)-7-Benzyl-7-aza-bicyclo[2.2.1]hept-2-yl)-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone 
• 2051-97-0 1-benzyl-1H-pyrrole 

Relevant articles and documents

Efficient generation and [3+2] cycloaddition of cyclic azomethine ylides: A general synthetic route to x-azabicyclo (m.2.1) alkane framework

An efficient method of cyclic azomethine ylide generation and their application in synthesizing x-azabicylo (m.2.1) alkanes has been described.

Stereoselective construction of X-azabicyclo[m.2.1]alkanes by [3+2]-cycloaddition of non-stabilized cyclic azomethine ylides: Synthesis of enantiopure constrained amino acids and formal total synthesis of optically active epibatidine

A new and general strategy for the stereoselective construction of X-azabicyclo[m.2.1]alkanes has been developed by the [3+2]-cycloaddition of cyclic azomethine ylides with suitable achiral dipolarophiles. The cyclic azomethine ylides, where the whole of the ylide conjugation is in the ring, have been generated by the sequential double desilylation of the N-alkyl-α,α′-bis(trimethylsilyl) cyclic amines utilizing Ag(I)F as one electron oxidant. The structural rigidity of cyclic azomethine ylides has allowed preferential facial discrimination by the dipolarophile resulting into very good exolendo selectivity. The exolendo selectivity associated with these cycloadditions has been further exploited to access optically pure X-azabicyclo[m.2.1]alkanes by carrying out the cycloadditions with the Oppolzer's acryloyl dipolarophile. Application of this methodology is demonstrated by the construction of few constrained amino acids related to azabicyclic structural framework and the formal total synthesis of optically active epibatidine.

2-Nitro Derivatives of the Alkaloid Epibatidine

2-Nitro-3-aryl-7-azabicyclo[2.2.1]heptanes 4, 18 have been synthesized by [1,3]-dipolar cycloadditions of cyclic unstabilized azomethine ylides 14 to β-nitro(hetero) styrenes 15, 17; in case of the pyridyl group the cycloadditions proceed stereoselectively to the exo-hetaryl products 4b,c. Introduction of an N-protecting formimidoyl group allows the regioselective synthesis of the N-substituted 2,5-bis(trimethylsilyl)pyrrolidines 12, 13 in high yields. The ylides 14 were generated by Ag+ mediated oxidation of these precursors.