54600-29-2

Usage

Type of compound

Pyrrolidine derivative

Structural feature

Contains a trimethylsilyl group attached to the methyl group of the pyrrolidine ring

Common use

Reagent in organic synthesis

Function

Protecting group for amines in chemical reactions

Property of trimethylsilyl group

Stabilizes reactive intermediates and enhances the selectivity of chemical transformations

Applications

Pharmaceutical, agrochemical, and material science industries

Value

Unique properties make it a valuable tool for synthetic chemists

Upstream product

• 123-75-1 pyrrolidine 
• 2344-80-1 Chloromethyltrimethylsilane 
• 584-08-7 potassium carbonate 

Downstream Products

• 37918-82-4 1-(3-phenylbut-3-en-1-yl)pyrrolidine 
• 442-52-4 clemizole 
• 2948-92-7 2-(pyrrolidin-1-ylmethyl)-1H-benzo[d]imidazole 
• 78064-96-7 4-(pyrrolidin-1-ylmethyl)benzonitrile 
• 60032-62-4 2-[(1-Pyrrolidinyl)methyl]pyridine 
• 3760-54-1 1-pyrrolidinecarboxaldehyde 
• 54600-35-0 N-(3-Butenyl)-N-trimethylsilylmethylanilin 

Relevant academic research and scientific papers

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.

Selective 1,2-Aryl-Aminoalkylation of Alkenes Enabled by Metallaphotoredox Catalysis

A highly chemo- and regioselective intermolecular 1,2-aryl-aminoalkylation of alkenes by photoredox/nickel dual catalysis is described here. This three-component conjunctive cross-coupling is highlighted by its first application of primary alkyl radicals, which were not compatible in previous reports. The readily prepared α-silyl amines could be transferred to α-amino radicals by photo-induced single electron transfer step. The radical addition/cross-coupling cascade reaction proceeds under mild, base-free and redox-neutral conditions with good functional group tolerance, and importantly, provides an efficient and concise method for the synthesis of structurally valuable α-aryl substituted γ-amino acid derivatives motifs.

An approach to some spiro oxindole alkaloids through cycloaddition reactions of 3-methylideneindolin-2-one

3-Methylideneindolin-2-one (3-methylideneoxindole) (1) was prepared in 60-89% yield by flash vacuum pyrolysis of the acetate or methyl carbonate of 3-hydroxy-3-methylindolin-2-one, and was fully characterized, but application of the same procedure to 3-hydroxy-5-methoxyindolin-2-one did not give useful yields. Cycloaddition reactions of CH2=+NR-CH2- and of the related ylide (25) (from 1-(trimethylsilylmethyl)piperidine-2-carbonitrile and AgF) to 3-methylideneindolin-2-one (1) gave 4-20% yields of spiro oxindoles, but yields were markedly below those achieved in cycloadditions to the more electrophilic N-phenylmaleimide (70-79%). Attempted alkylation of weakly basic secondary amines, e.g. piperidine-2-carbonitrile, with Me3SiCH2Cl in dimethyl sulfoxide/K2CO3 gave only carbamates Me3SiCH2OOCNR2. CSIRO 2000.