921224-82-0

Usage

Uses

Used in Medicinal Chemistry:
2-(Trifluoromethyl)-D-proline is used as a building block for the synthesis of new drugs due to its unique structural and chemical properties. The trifluoromethyl group enhances the potency and selectivity of pharmaceutical compounds, making it an attractive component in drug design.
Used in Drug Development:
2-(Trifluoromethyl)-D-proline is utilized as a valuable tool in the development of novel pharmaceutical agents. The D configuration of 2-(Trifluoromethyl)-D-proline can confer specific biological and pharmacological activities, which are crucial for the creation of effective and targeted therapeutics.

Upstream product

• 921224-77-3 (3S,5R)-3-allyl-3-trifluoromethyl-5-phenylmorpholin-2-one 
• 921224-81-9 (4R,8aS)-8a-trifluoromethyl-4-phenyl-hexahydro-pyrrolo[2,1-c][1,4]oxazin-1-one 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 

Downstream Products

• 921224-83-1 (S)-α-trifluoromethyl-prolinol 

Relevant academic research and scientific papers

Synthesis of enantiopure α-Tfm-proline and α-Tfm-pipecolic acid from oxazolo-pyrrolidines and -piperidines

Enantiopure α-Tfm-proline and α-Tfm-pipecolic acid were synthesized starting from commercially available diesters and ethyl trifluoroacetate. A Strecker type reaction on intermediate chiral Tfm-oxazolo-pyrrolidine and -piperidine provided the corresponding nitrile precursor of enantiopure (R) and (S) α-Tfm-proline and α-Tfm-pipecolic acid. The C-terminal peptide coupling reaction of α-Tfm-pipecolic acid has been successfully achieved.

Synthesis of an MIF-1 analogue containing enantiopure (S)-α- trifluoromethyl-proline and biological evaluation on nociception

The synthesis and the effect of a novel MIF-1 analogue on nociception during acute pain in rat model are reported. The synthesis of this enantiopure trifluoromethyl group containing tripeptide was performed through a peptide coupling reaction between the HCl. Leu-Gly-NH2 and the (S)-α-Tfm-proline. The analgesic effect of the CF3-(MIF-1) 2 has been evaluated in vivo on rat model by paw pressure (PP) and hot plate (HP) tests and compared to the native peptide MIF-1. Highest analgesic effect was observed with CF3-(MIF-1) 2 only in PP test. In order to study the mechanisms of nociception induced by the studied peptides, the involvement of the opioid and the nitric oxideergic systems was investigated. The results are in favor of a participation of both system since pretreatment, 20 min before injection of the CF3-(MIF-1) 2, with the non-competitive antagonist of opiate receptors naloxone, the nitric oxide synthase (NOS) inhibitor l-N G-nitroarginine ester (l-NAME) or the nitric oxide (NO) donor l-arginine (l-Arg) significantly decreased the pain perception in PP and HP tests.

Iodocyclization of chiral cf3-allylmorpholinones: A versatile strategy for the synthesis of enantiopure α-Tfm-prolines and α-Tfm-dihydroxyprolines

An efficient iodocyclization reaction of a chiral Tfm-allylmorpholinone provides a straightforward route to α-Tfm-prolines and α-Tfmdihydroxyprolines. The methodologies developed are particularly well adapted for gram-scale synthesis of enantiopure compou

Convenient synthesis of N-Terminal Tfm-Dipeptides from unprotected enantiopure α-Tfm-Proline and α-Tfm-alanine

A convenient procedure for the synthesis of highly lipophilic dipeptide building blocks from enantiopure α-trifluoromethyl α-amino acids is reported. Coupling reactions at the C termini of the trifluoromethyl a-amino acids were successfully performed with

Straightforward synthesis of (S)- and (R)-α-trifluoromethyl proline from chiral oxazolidines derived from ethyl trifluoropyruvate

(Chemical Equation Presented) A concise synthesis of both enantiomers of α-Tfm-proline and (S)-α-Tfm-prolinol from ethyl trifluoropyruvate is reported. The key step is a diastereoselective allylation reaction of ethyl trifluoropyruvate and (R)-phenylglyci