124391-76-0

Usage

Uses

Used in Organic Synthesis:
(S)-1-CBZ-3-HYDROXYMETHYLPYRROLIDINE is used as a chiral building block for the synthesis of various organic compounds. Its unique structure allows for the creation of enantiomerically pure products, which is crucial in many chemical reactions where stereochemistry plays a significant role.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (S)-1-CBZ-3-HYDROXYMETHYLPYRROLIDINE is used as a key intermediate in the development of new drugs. Its chiral nature and functional groups make it a valuable component in the synthesis of biologically active molecules, potentially leading to the discovery of novel therapeutic agents.
Used in Chiral Chemistry:
(S)-1-CBZ-3-HYDROXYMETHYLPYRROLIDINE is utilized in chiral chemistry for the study of enantiomers and their distinct properties. Understanding the behavior of these mirror-image forms can provide insights into the development of enantioselective catalysts and the design of enantiomerically pure compounds with specific biological activities.
The specific applications and effects of (S)-1-CBZ-3-HYDROXYMETHYLPYRROLIDINE in these fields are still being explored, and ongoing research may uncover additional uses and benefits of (S)-1-CBZ-3-HYDROXYMETHYLPYRROLIDINE.

InChI:InChI=1/C13H17NO3/c15-9-12-6-7-14(8-12)13(16)17-10-11-4-2-1-3-5-11/h1-5,12,15H,6-10H2/t12-/m0/s1

Upstream product

• 192213-99-3 (S)-1-Benzyl-3-benzyloxymethyl-pyrrolidine 
• 172796-28-0 (R)-4-((benzyloxy)methyl)dihydrofuran-2(3H)-one 
• 78914-69-9 (S)-(-)-N-benzylpyrrolidine-2-methanol hydrochloride 
• 617-52-7 Dimethyl itakonate 
• 99735-46-3 methyl (3S)-1-<(R)-1-phenylethyl>-5-oxo-3-pyrrolidinecarboxylate 
• 501-53-1 benzyl chloroformate 
• 110013-19-9 (S)-(-)-3-(hydroxymethyl)pyrrolidine 
• 31970-04-4 1-carboxybenzyl-3-pyrrolidine 
• 74-97-5 chlorobromomethane 
• 192213-98-2 Methanesulfonic acid (R)-2-benzyloxymethyl-4-methanesulfonyloxy-butyl ester 
• 192213-97-1 (S)-2-Benzyloxymethyl-butane-1,4-diol 

Downstream Products

• 72580-53-1 (S)-(+)-3-pyrrolidinecarboxylic acid 
• 847952-27-6 (S)-3-{4-[(S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-pyrrolidine-1-carboxylic acid benzyl ester 
• 648418-11-5 (S)-3-(4-Benzyloxycarbonylamino-2-fluoro-phenoxymethyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 790702-94-2 N-{(S)-3-[3-Fluoro-4-((S)-1-pyrrolidin-3-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide 
• 192214-00-9 (S)-1-((benzyloxy)carbonyl)pyrrolidine-3-carboxylic acid 

Relevant academic research and scientific papers

A rapid and convenient synthesis of β-proline

A short, reliable, and cheap synthesis of both enantiomers of β-proline, an efficient organocatalyst and an important building block in medicinal chemistry, has been developed in four steps (overall yield: 72%) from the diasteromeric adducts of methyl itaconate and (R)-α-methylbenzylamine. The key step involves the chemoselective reduction of a lactam group in the presence of a benzyl ester.

Method of treating addiction or dependence using a ligand for a monoamine receptor or transporter

One aspect of the present invention relates to a method of treating of drug addiction or drug dependence in a mammal, comprising the step of administering to a mammal in need thereof a therapuetically effective amount of a heterocyclic compound, e.g., a 3-substituted piperidine. In a preferred embodiment, the method of the present invention treats cocaine addiction or methamphetamine addiction.

Ligands for monoamine receptors and transporters, and methods of use thereof

One aspect of the present invention relates to heterocyclic compounds. A second aspect of the present invention relates to the use of the heterocyclic compounds as ligands for various mammalian cellular receptors, including dopamine, serotonin, or norepinephrine transporters. The compounds of the present invention will find use in the treatment of numerous ailments, conditions and diseases which afflict mammals, including but not limited to addiction, anxiety, depression, sexual dysfunction, hypertension, migraine, Alzheimer's disease, obesity, emesis, psychosis, schizophrenia, Parkinson's disease, inflammatory pain, neuropathic pain, Lesche-Nyhane disease, Wilson's disease, and Tourette's syndrome. An additional aspect of the present invention relates to the synthesis of combinatorial libraries of the heterocyclic compounds, and the screening of those libraries for biological activity, e.g., in assays based on dopamine transporters.

CHIRAL SYNTHESIS VIA ORGANOBORANES. 19. THE SUCCESSFUL ONE-CARBON HOMOLOGATION OF HETEROCYCLIC BORONATE ESTERS WITH HIGH OPTICAL PURITY

An exploratory study was undertaken to establish the applicability of the one-carbon homologation to heterocyclic boronic esters.This procedure involves the use of (cloromethyl)lithium, LiCH2Cl, generated in situ by the reaction of bromochloromethane and n-BuLi in THF at -78 deg C in the presence of an enantiomerically pure heterocyclic boronic ester.These heterocyclic boronic esters were prepared via asymmetric hydroboration of representative heterocyclic olefins bearing either an endocyclic or exocyclic double bond with either Ipc2BH or IpcBH2 in THF.