52321-06-9

Basic information

• Product Name: diethyl 1-benzylpyrrolidine-2,5-dicarboxylate
• Synonyms: Nsc143948;(2S,5R)-Diethyl 1-benzylpyrrolidine-2,5-dicarboxylate
• CAS NO: 52321-06-9
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.37
• Mol File: 52321-06-9.mol

Chemical Properties

• Melting Point: 123-125 °C
• Boiling Point: 145-148 °C(Press: 0.3 Torr)
• Appearance: /
• Density: 1.146±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 5.83±0.60(Predicted)
• CAS DataBase Reference: diethyl 1-benzylpyrrolidine-2,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl 1-benzylpyrrolidine-2,5-dicarboxylate(52321-06-9)
• EPA Substance Registry System: diethyl 1-benzylpyrrolidine-2,5-dicarboxylate(52321-06-9)

Safety Data

• Hazardous Substances Data: 52321-06-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl 1-benzylpyrrolidine-2,5-dicarboxylate is used as a pharmaceutical intermediate for the synthesis of various drugs due to its complex molecular structure and potential biological activities.
Used in Medication Development:
It is used as a building block in the development of new medications, particularly for its anticonvulsant and anti-inflammatory properties.
Used as an Analgesic Agent:
Diethyl 1-benzylpyrrolidine-2,5-dicarboxylate is studied for its potential use as an analgesic agent, providing pain relief for various conditions.
Used as an Anesthetic Agent:
It is also being studied for its potential use as an anesthetic agent, which can be utilized in medical procedures to induce a temporary loss of sensation or awareness.

Upstream product

• 111-50-2 Adipic acid dichloride 
• 17740-40-8 diethyl meso-1-benzyl-2,5-pyrrolidinedicarboxylate 
• 869-10-3 diethyl 2,5-dibromoadipate 
• 100-46-9 benzylamine 
• 137300-49-3 (2R,5S)-2,5-Dibromo-hexanedioyl dichloride 
• 124-04-9 Adipic acid 
• 29548-86-5 2,5-dibromohexanedioyl dichloride 
• 90290-04-3 trans-N-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine 
• 54221-37-3 diethyl meso-2,5-dibromoadipate 

Downstream Products

• 90290-04-3 trans-N-benzyl-2,5-bis(ethoxycarbonyl)pyrrolidine 
• 191850-97-2 cis-1-benzyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate 

Relevant articles and documents

Streamlined Synthesis of a Bicyclic Amine Moiety Using an Enzymatic Amidation and Identification of a Novel Solid Form

We describe a series of improvements to the synthesis of a 3,8-diazabicyclo[3.2.1]octane derivative that result in a reduced step count and higher overall efficiency compared to previously published syntheses. Our method includes optimization and mechanistic understanding of a key diastereoselective cyclization to achieve a >95:5 diastereomeric ratio, as well as demonstration of a unique enzyme-catalyzed amidation reaction using hexamethyldisilazane as both an ammonia source and scavenger. Finally, we identify a novel cocrystal solid form of the target compound that provides improved purity and material properties. Demonstration of the new chemistry to prepare >100 kg of the target compound serves to illustrate the robustness of the new process.

Synthesis of bridged bicyclic amino alcohols as compact modules for medicinal chemistry

The efficient synthetic routes of three bridged bicyclic amino alcohols were reported. It is conceivable that these compounds could be readily used as compact modules in medicinal chemistry to fine-tune physicochemical and pharmacokinetic properties, in order to eventually improve the overall quality of small molecule drug candidates.

INHIBITORS OF THE BCL6 BTB DOMAIN PROTEIN-PROTEIN INTERACTION AND USES THEREOF

The present application relates to compounds of Formula I (I) or pharmaceutically acceptable salts, solvates and/or prodrugs thereof, to compositions comprising these compounds or pharmaceutically acceptable salts, solvates and/or prodrugs thereof, and various uses in the treatment of diseases, disorders or conditions that are treatable by inhibiting interactions with BCL6 BTB, such as cancer.

SUBSTITUTED PHENYLOXAZOLIDINONES FOR ANTIMICROBIAL THERAPY

The present invention relates to novel oxazolidinones (Formula I): or a pharmaceutically acceptable salt having ring A characterized by N-containing monocyclic, bicyclic or spirocyclic substituents, to their preparation, and to their use as drugs for treating Mycobacterium tuberculosis and other microbial infections, either alone or in combination with other anti-infective treatments.

Pyruvate kinase activators for use in therapy

Described herein are methods for using compounds that activate pyruvate kinase.

ALPHA-UNSUBSTITUTED ARYLMETHYL PIPERAZINE PYRAZOLO[1,5-A] PYRIMIDINE AMIDE DERIVATIVES

Methods of preventing, treating or delaying the onset of HIV in a subject by administering to the subject novel pharmaceutically active arylmethyl pyrazolo[1,5-α ]pyrimidine amide derivatives, or pharmaceutical compositions containing the same are described. Additionally, compounds of novel pharmaceutically active arylmethyl piperazine pyrazolo[l,5-α]pyrimidine amide derivatives and their use for the manufacture of specific medicaments are described.

Bicyclic piperazines as metabotropic glutatmate receptor antagonists

The invention relates to compounds of formula I or pharmaceutically acceptable salts or solvates thereof: where Ar1, A, Hy, R1, m and n are as defined in the description. The invention also includes pharmaceutical compositions and uses of, and processes of making the compounds, as well as methods of medical treatment of mGluR5-mediated disorders.

cis-2,5-dicyanopyrrolidine inhibitors of dipeptidyl peptidase IV: Synthesis and in vitro, in vivo, and x-ray crystallographic characterization

Inhibitors of the glucagon-like peptide-1 (GLP-1) degrading enzyme dipeptidyl peptidase IV (DPP-IV) have been shown to be effective treatments for type 2 diabetes in animal models and in human subjects. A novel series of cis-2,5-dicyanopyrrolidine α-amino amides were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-IV) for the treatment of type 2 diabetes. 1-({[1-(Hydroxymethyl)cyclopentyl]amino}-acetyl)pyrrolidine-2,5-cis- dicarbonitrile (1c) is an achiral, slow-binding (time-dependent) inhibitor of DPP-IV that is selective for DPP-IV over other DPP isozymes and proline specific serine proteases, and which has oral bioavailability in preclinical species and in vivo efficacy in animal models. The mode of binding of the cis-2,5-dicyanopyrrolidine moiety was determined by X-ray crystallography. The hydrochloride salt of 1c was further profiled for development as a potential new treatment for type 2 diabetes.

Synthesis and Structure-Activity Relationship of Di-(3,8-diazabicyclo[3.2.1]octane) Diquaternary Ammonium Salts as Unique Analgesics

Based on the structure characteristics of the lead compounds, 1,1′2-octanedioyl-4,4′-dimethyl-4,4′-dibenzyl dipiperazinium dibromide (2) and 3,8-disubstituted-3,8-diazabicyclo[3.2.1]octanes (DBO), di-(3,8-diazabicyclo[3.2.1]octane) diquaternary ammonium salts 3 a-c were designed and synthesized through a highly practical procedure. Target compounds 3 a-c and the hydrochloride salts of their precursors 10 a-c were evaluated for their in vivo analgesic and sedative activities. Interestingly, the introduction of an endoethylenic bridge in the piperazine of lead compound 2 causes loss of the analgesic activity and increases the toxicity dramatically. This result shows that the flexible conformation of piperazine in compound 2 is favorable for interaction with the receptor, and the quaternization of compounds 10 a-c is the main reason for the toxicity increase.

N-benzenesulfonyl l-proline compounds as bradykinin antagonists

This invention provides a compound of the formula (I): or the pharmaceutically acceptable salts thereof wherein X1 and X2 are halo; R1 and R2 are independently hydrogen or C1-4 alkyl; R3 and R4 are each hydrogen or halo; and R5 is (a) —C3-9 diazacycloalkyl optionally substituted with C5-11 azabicycloalkyl; (b) —C3-9 azacycloalkyl-NH—(C5-11 azabicycloalkyl optionally substituted with C1-4 alkyl); (c) —NH—C1-3 alkyl-C(O)—C5-11 diazabicycloalkyl; (d) —NH—C1-3 alkyl-C(O)—NH—C5-11 azabicycloalkyl, the C5-11 azabicycloalkyl being optionally substituted with C1-4 alkyl; (e) —C3-9 azacycloalkyl optionally substituted with C3-9 azacycloalkyl; or (f) —NH—C1-5 alkyl-NH—C(O)—C4-9 cycloalkyl-NH2. These compounds are useful for the treatment of medical conditions mediated by bradykinin such as inflammation, allergic rhinitis, pain, etc. This invention also provides a pharmaceutical composition comprising the above compound.