78027-57-3

Usage

Uses

Used in Pharmaceutical Industry:
1-BENZYL-3-HYDROXY-PYRROLIDINE-2,5-DIONE is used as a building block in organic synthesis for the development of new pharmaceutical compounds. Its unique structure and potential biological activities, such as anti-inflammatory and antioxidant effects, make it a valuable component in the creation of novel drugs with therapeutic benefits.
Used in Medicinal Chemistry Research:
1-BENZYL-3-HYDROXY-PYRROLIDINE-2,5-DIONE is employed as a key intermediate in the synthesis of various bioactive molecules. Its presence in the molecular structure can contribute to the modulation of pharmacological properties, making it an essential component in medicinal chemistry research aimed at discovering and optimizing new therapeutic agents.
Used in Drug Discovery:
1-BENZYL-3-HYDROXY-PYRROLIDINE-2,5-DIONE is utilized in drug discovery processes to explore its potential as a lead compound for the treatment of various diseases. Its structural features and biological activities are investigated to identify its therapeutic potential and to guide the design of more effective and targeted drugs.
Overall, 1-BENZYL-3-HYDROXY-PYRROLIDINE-2,5-DIONE's applications in the pharmaceutical industry, medicinal chemistry research, and drug discovery highlight its significance in the development of innovative and effective therapeutic agents.

Upstream product

• 1028903-71-0 N-benzyl-(3S,4R)-3,4-dihydroxy-2,5-pyrrolidinedione 
• 97-67-6 (S)-Malic acid 
• 100-46-9 benzylamine 
• 617-48-1 malic acid 
• 141650-65-9 (+/-)-N-benzyl-2-hydroxy-succinamic acid 

Downstream Products

• 129823-21-8 3-acetoxy-1-benzyl-2,5-pyrrolidinedione 
• 775-15-5 1-benzyl-3-pyrrolidinol 
• 224561-57-3 1-benzyl-2-hydroxy-5-oxopyrrolidin-3-yl acetate 
• 130781-06-5 Acetic acid 1-benzyl-2-ethoxy-5-oxo-pyrrolidin-3-yl ester 
• 170711-06-5 1-Benzyl-4-benzyloxy-5-hydroxy-pyrrolidin-2-one 
• 328047-13-8 Acetic acid 3-acetoxy-1-benzyl-5-oxo-pyrrolidin-2-yl ester 
• 130781-10-1 1-Benzyl-4-benzyloxy-5-ethoxy-pyrrolidin-2-one 
• 130781-12-3 Acetic acid 1-benzyl-3-benzyloxy-5-oxo-pyrrolidin-2-yl ester 
• 130781-14-5 Acetic acid (2R,3R)-2-allyl-1-benzyl-5-oxo-pyrrolidin-3-yl ester 
• 130781-14-5 Acetic acid (2R,3S)-2-allyl-1-benzyl-5-oxo-pyrrolidin-3-yl ester 
• 130781-16-7 5-Allyl-1-benzyl-4-benzyloxy-pyrrolidin-2-one 
• 38116-01-7 malic acid N,N'-dibenzyldiamide 

Relevant academic research and scientific papers

Metal-Free Iodine-Mediated Deoxygenation of Alcohols in the Position α to Electron-Withdrawing Groups

The use of a substoichiometric amount of molecular iodine in the presence of PPh3 and pyridine effects a direct deoxygenation of primary and secondary alcohols in positions α to a variety of activating electron-withdrawing groups, including ketones, esters, amides, imides and nitrile groups.

Metal-free Hydroalkoxylation-Formal [4+2] Cycloaddition Cascade for the Synthesis of Ketals

A transition metal free, acid promoted cascade hydroalkoxylation–formal [4+2] cycloaddition of various alkynols with salicylaldehyde is demonstrated for the synthesis of tetrahydrofurano/pyrano-chromenes and spiroketals. In general, alkynols underwent hydroalkoxylations in an endo-dig manner when internal alkynes were used to furnish the heteroannular ketals, whereas terminal alkynes proceeded in an exo-dig fashion leading to spiroketals. The study revealed that intramolecular hydroalkoxylation of alkynols is a preferred path over a generation of oxonium ions when coupling partner is salicylaldehyde. This metal-free transformation provides a new avenue for the stereoselective synthesis of tetrahydrofurano- and pyrano-chromenes in an expeditious manner.

Thermal reactions of malic acid benzylamine salts

Malic acid, a component present in fruit, is known to be an important precursor for the prebiotic formation of polyaspartic acid. Malic acid is a dicarboxylic acid, possessing one hydroxyl group. It yields many types of crystalline salts with amino compounds. Although the thermal reactions of the amino salts have been reported, their dehydration reaction pathway has not been studied. This paper describes the dehydration process using thermal gravimetry and differential thermal analysis. The results show that the malic acid monobenzylamine and the dibenzylamine salts release water molecules during an endothermic reaction to afford malic acid benzylimide and malic acid dibenzylamide, respectively. The latter compound is stable up to 230 °C.

Synthesis of racemic and enantiomeric 3-pyrrolidinyl derivatives of nucleobases

The synthesis of novel 3-pyrrolidinyl derivatives of nucleobases is described. Starting from malic acid, we improved the synthesis of both racemic and optically active N-benzyl-3-hydroxypyrrolidine-2,5-diones, which were transformed in four steps into N-tert-butyloxycarbonyl-3-mesyloxypyrrolidines, the key synthons for the alkylation of purine and pyrimidine nucleobases. Alkylations of cesium salts of purines and sodium salts of pyrimidines with N-tert-butyloxycarbonyl-3-mesyloxypyrrolidines proceeded smoothly, giving high yields of 9-substituted purine derivatives and moderate yields of 1-substituted pyrimidine derivatives. Using (S)-N-tert-butyloxycarbonyl-3-mesyloxypyrrolidine as the same intermediate for the synthesis of both enantiomeric N-Boc-3-pyrrolidinyladenines, and considering the results obtained on chiral HPLC analysis of the products, we proved that nucleophilic displacement of the mesyloxy group proceeded with inversion and not with retention of the configuration. Prepared compounds were tested for cytostatic and antiviral properties, but no significant activity was found.

Direct synthesis of imides from dicarboxylic acids using microwaves

1,4- and 1,5-dicarboxylic acids, when treated with amines in a domestic microwave oven, afford good yields of the corresponding imides.

Lipase-catalyzed practical synthesis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its related compounds

A practical method for preparing (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione (1) was investigated by the use of the enzymatic hydrolysis of its acetate (2a). Among several hydrolases examined here, lipase PS from Pseudomonas cepacia gave the best result: In a mixed solvent (1:1 v/v) of dioxane and a phosphate buffer (pH 7), the hydrolysis took place smoothly with a high enantioselectivity (E > 3000). Several 3-alkanoyl derivatives of 1 were subjected to the lipase PS-catalyzed hydrolysis. The chain length of the alkanoyl does not noticeably influence the reaction rate or the enantioselectivity. In contrast, the hydrolysis of the 1-benzoyl derivative proceeded slowly with a low enantioselectivity (E = 19). The syntheses of optically active 3-hydroxypyrrolidines and 3-hydroxypiperidines were also achieved under the reaction conditions similar to the lipase PS-catalyzed hydrolysis of 2a.

Stereoselective synthesis of statin analogues

Statin analogues can be synthesized stereoselectively (diastereomeric ratios up to 4:1) starting from malic acid. The key step involves an unprecedented cis-selective allylation of an α-alkoxy N-acyliminium ion.

SYNTHETIC ROUTES TO 3-PYRROLIDINOL

Short, convenient routes to 3-pyrrolidinol are described.