194924-95-3

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Pyrrolidinedicarboxylic acid, 4-oxo-, 1-(1,1-diMethylethyl) 3-Methyl ester is used as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 1,3-Pyrrolidinedicarboxylic acid, 4-oxo-, 1-(1,1-diMethylethyl) 3-Methyl ester is utilized as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its reactivity and versatility contribute to the development of effective and environmentally friendly solutions for agricultural challenges.
Used in Flavor Industry:
1,3-Pyrrolidinedicarboxylic acid, 4-oxo-, 1-(1,1-diMethylethyl) 3-Methyl ester is also employed in the flavor industry as a key component in the creation of various flavors. Its unique chemical properties enable the development of novel and innovative flavor profiles for food and beverage products.

Upstream product

• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 1309676-07-0 N-(1-tert-butyloxycarbonyl-3-methoxycarbonyl-2,5-dihydropyrrol-4-yl)-L-valine diethylamide 
• 120871-73-0 3-allyl-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Preparation of new 1,4-diazocanes as scaffolds for combinatorial chemistry

Hexahydro-2-oxo-1,4-diazocin-6-carboxylic acid constitutes a conformationally rigid, crown-shaped scaffold. An orthogonally protected (Boc at N-4 and methyl ester at 6-CO2H) representative was prepared by ring expansion of a 3-pyrrolidone-derived 1,4-diketone with MeNH2. After deprotection, this building block was further diversified by reductive aminations and amidations and by sulfonamide and urea formation. Furthermore, the 6-CO2H function was transformed into a 6-NHCbz group in one step by carboxamide degradation in the presence of BnOH. An example of a cyclic tripeptoidic structure was synthesized by amidation with N-Boc-β-alanine and glycine methyl ester. Structural features of the eight-membered heterocycle were established by single-crystal X-ray structure analysis of a 4-bromoaniline derivative.

Enantioselective synthesis of hexahydroisobenzofuran and hexahydro-isoindole derivatives with quaternary stereocenters

Oxo esters with pyrrolidine and tetrahydrofuran rings were converted into optically active isobenzofuran and isoindole derivatives. The key step of the sequence was a copper-catalyzed asymmetric Michael reaction with methyl vinyl ketone and en-amines prepared from the oxo esters and l-valine diethylamide. The chiral auxiliary was cleaved from the products during workup and 1,5-diketones with a quaternary stereocenter are obtained with 97-99% ee. Subsequent annulation reactions were achieved in two steps via the intermediate aldol products. Georg Thieme Verlag Stuttgart - New York.

Total synthesis of (-)-slaframine from (2R,3S)-3-hydroxyproline

The yeast reduction products (2R,3S)-N-Boc-3-hydroxyproline esters 23 have been converted into the 3-methoxymethoxyprolinal 26 which undergoes an efficient Julia olefination with the L-serine-derived amino sulfone 29. Selective reduction of the resulting alkene 31 using diimide and cyclization leads to N-(benzyloxycarbonyl)slaframine 33c and thence to natural (-)-slaframine 5 and its more stable, crystalline N-acetyl derivative 34.