169774-59-8

Upstream product

• 31560-20-0 (2S,4R)-1-benzoyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester 
• 98-88-4 benzoyl chloride 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 

Downstream Products

• 1318129-29-1 (S)-2-(azidomethyl)-1-benzyl-4,4-difluoropyrrolidine 
• 1318129-26-8 (R)-5-azido-1-benzyl-3,3-difluoropiperidine 
• 1318130-03-8 (S)-methyl 4,4-difluoro-1-(phenylcarbonyl)pyrrolidine-2-carboxylate 
• 1318129-12-2 (S)-(1-benzyl-4,4-difluoropyrrolidin-2-yl)methanol 
• 169774-61-2 (2S,3R)-1-benzoyl-3-tert-butoxycarbonylmethyl-4-oxopyrrolidine-2-carboxylic acid methyl ester 
• 171897-42-0 methyl (2R,4R)-1-benzoyl-4-(4-chlorophenyl)-4-hydroxy-2-pyrrolidinecarboxylate 
• 171897-37-3 methyl (2S,4R)-1-benzoyl-4-(4-chlorophenyl)-2-pyrrolidinecarboxylate 
• 171897-43-1 methyl (2R,4S)-1-benzoyl-4-(4-chlorophenyl)-2-pyrrolidinecarboxylate 
• 171897-44-2 (2R,4S)-4-(4-chlorophenyl)-2-pyrrolidinecarboxylic acid 
• 171897-38-4 (2S,4R)-4-(4-chlorophenyl)-2-pyrrolidinecarboxylic acid 
• 169774-63-4 (2S,3R)-1-Benzoyl-3-tert-butoxycarbonylmethyl-4-trifluoromethanesulfonyloxy-2,3-dihydro-1H-pyrrole-2-carboxylic acid methyl ester 
• 169774-67-8 (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2-methoxyphenyl)-<4,5>-dehydropyrrolidine 
• 169774-69-0 (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(3-methoxyphenyl)-<4,5>-dehydropyrrolidine 
• 169774-71-4 (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(4-methoxyphenyl)-<4,5>-dehydropyrrolidine 

Relevant academic research and scientific papers

Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands

(-)-Kainic acid potently increases stretch-induced afferent firing in muscle spindles, probably acting through a hitherto uncloned phospholipase D (PLD)-coupled mGlu receptor. Structural modification of (-)-kainic acid was undertaken to explore the C-4 substituent effect on the pharmacology related to muscle spindle firing. Three analogues 1a-c were synthesised by highly stereoselective additions of a CF3, a hydride and an alkynyl group to the Re face of the key pyrrolidin-4-one intermediate 5a followed by further structural modifications. Only the 4-(1,2,3-triazolyl)-kainate derivative 1c retained the kainate-like agonism, increasing firing in a dose-dependent manner. Further modification of 1c by introduction of a PEG-biotin chain on the 1,2,3-triazole fragment afforded compound 14 which retained robust agonism at 1 μM and appears to be suitable for future use in pull-down assays and far western blotting for PLD-mGluR isolation. This journal is

Towards a versatile synthesis of kainoids I: Introduction of the C-3 and C-4 substituents

The first stages in the synthesis of acromelic acid analogues from trans-4-hydroxy-L-proline are described. An enamine alkylation was used to stereospecifically introduce the C-3 substituent, Grignard addition to a ketone or Pd(0) catalysed cross-coupling procedures adding C-4 aryl substituents for further manipulation. A number of versatile intermediates were generated.

Method for the preparation of N-substituted 4-ketoproline derivatives

Method for the preparation of N-protected 4-ketoproline derivatives of formula I STR1 by oxidation of the corresponding N-protected 4-hydroxyproline derivatives of STR2 using the system TEMPO (2,2,6,6-tetramethylpiperidinyl oxy free radical)/NaOCl.

Stereospecific synthesis of (R)- and (S)-Baclofen and (R)- and (S)- PCPGABA [4-amino-2-(4-chlorophenyl)butyric acid] via (R)- and (S)-3-(4- chlorophenyl)pyrrolidines

(R)- and (S)-baclofen and (R)- and (S)-PCPGABA [4-amino-2-(4- chlorophenyl)butyric acid] were stereospecifically synthesized via (R)- and (S)-3-(4-chlorophenyl)pyrrolidines, starting from trans-4-hydroxy-L-proline. The syntheses involve two key operations

A versatile approach to acromelic acid analogues

A route to acromelic acid analogues and their corresponding C-4 epimers from trans-4-hydroxy-L-proline is described. The C-4 substituent was introduced by a Suzuki-type boronate coupling to a vinyl triflate.