393154-87-5

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4R)-tert-butyl 4-hydroxypyrrolidine-2-carboxylate is utilized as a chiral building block in the pharmaceutical industry for the synthesis of various drugs. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which is crucial for the development of effective and safe medications.
Used in Agrochemical Industry:
In the agrochemical sector, (2S,4R)-tert-butyl 4-hydroxypyrrolidine-2-carboxylate serves as a key intermediate in the synthesis of biologically active compounds. Its chiral properties enable the production of enantiomerically pure agrochemicals, which can help improve the efficacy and selectivity of these products.
Used in Materials Science:
(2S,4R)-tert-butyl 4-hydroxypyrrolidine-2-carboxylate is also employed in materials science for the development of novel materials with specific properties. Its unique structure and stereochemistry contribute to the creation of materials with tailored characteristics for various applications.
Used in Organic Synthesis:
As a versatile chiral building block, (2S,4R)-tert-butyl 4-hydroxypyrrolidine-2-carboxylate is extensively used in organic synthesis for the preparation of a wide range of organic compounds. Its reactivity and stereochemistry make it a valuable component in the synthesis of complex organic molecules.

Upstream product

• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 72289-52-2 (2S,4R)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester 

Downstream Products

• 159487-56-6 N-<(2S,4S)-4-<2-(tert-Butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>-N-<(2S,4S)-4-<1-(benzyloxycarbonyl)-2-(tert-butoxycarbonyl)pyrrolidinyl>>amine 
• 159487-59-9 N,N-Bis<(2S,4S)-4-<2-(tert-butoxycarbonyl)-1-<(tert-butoxycarbonyl)methyl>pyrrolidinyl>>glycine benzyl ester 
• 171192-76-0 (2S,4S)-1-benzyl-2-tert-butoxycarbonylpyrrolidine-4-spiro-5'-hydantoin 
• 171336-74-6 (2S,4R)-1-benzyl-2-tert-butoxycarbonylpyrrolidine-4-spiro-5'-hydantoin 
• 171192-78-2 methyl (2S,4S)-4-amino-1-benzyl-4-methoxycarbonylprolinate 
• 171336-82-6 methyl (2S,4R)-4-amino-1-benzyl-4-methoxycarbonylprolinate 
• 171336-75-7 (2S,4S)-4-amino-1-benzyl-4-carboxyproline 
• 171336-77-9 (2S,4R)-4-amino-1-benzyl-4-carboxyproline 
• 171336-79-1 (2S,4S)-4-amino-4-carboxyproline 
• 171336-79-1 (2S,4R)-4-aminopyrrolidine-2,4-dicarboxylic acid 
• 171192-75-9 tert-butyl (2S)-1-benzyl-4-oxoprolinate 
• 171192-73-7 tert-butyl (2S,4R)-1-benzyl-4-hydroxyprolinate 

Relevant academic research and scientific papers

Asymmetric syntheses of all four isomers of 4-amino-4-carboxyproline: Novel conformationally restricted glutamic acid analogues

Asymmetric syntheses of all four isomers of 4-amino-4-carboxyprolines, i.e. (2S,4S)-3, (2S,4R)-4, and their corresponding enantiomers, as novel conformationally restricted analogues of glutamic acid, were performed from trans-4-hydroxy-L-proline as a homochiral starting material. The key step was the spirohydantoin ring formation by employing the Bucherer-Bergs reaction of 4-oxoproline derivatives. These structures were determined by NMR studies.

Synthesis of conformationally constrained DTPA analogues. Incorporation of the ethylenediamine units as aminopyrrolidines

The synthesis of conformationally constrained diethylenetriaminepentaacetic acid (DTPA) analogues is an effort to probe the relationship between ligand structure and metal complex stability. In the pursuit of this objective, diastereomerically and enantiomerically pure mono- and bis-pyrrolidine analogues of DTPA have been prepared from trans-4-hydroxy-L-proline. The mono-pyrrolidine chelator 1 was constructed from a single hydroxyproline unit and an ethylenediamine moiety while two hydroxyproline-derived fragments 4e or 14b and 9b were coupled by N-alkylation of a triflate to afford the core bis-pyrrolidine structures: optically active 10 and meso-15. Deprotection of the triamine pentaesters 12 and 17 afforded the triamine pentaacetic acids 2 and 3 as their hydrochloride salts. The stereochemical homogeneity of precursor esters 12 and 17 was determined by HPLC using authentic epimeric standards to establish that essentially no racemization of the original amino acid α-center had occurred. Some loss of stereochemical homogeniety was encountered in the synthesis of 10 and 15 by N-alkylation of aminoproline 9b with a hydroxyproline-derived triflate, which had proceeded with some retention of configuration. The diastereomeric impurities were removed by crystallization of the respective benzyl carbamates. Bis-pyrrolidine pentaacids 2 and 3 formed isolable chelates with gadolinium and lutetium. A comparision of the lutetium chelates of 2 and 3 by NMR revealed significant differences which were reflective of a rigid structure with 2, while metal complexation with 3 was structurally less defined.