116183-80-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine is used as a chiral auxiliary in the preparation of chiral amino acids and other pharmaceutical intermediates. Its ability to control stereochemistry is crucial for the synthesis of enantiomerically pure compounds, which are essential in the development of effective and safe drugs.
Used in Organic Synthesis:
(R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine serves as a versatile building block in organic synthesis, enabling the creation of a wide range of chiral compounds with specific stereochemistry. This property is valuable in the synthesis of complex organic molecules, including natural products and bioactive compounds.
Used in Catalysis:
(R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine has potential applications as a ligand in catalysis. Its chiral nature and ability to control stereochemistry make it a promising candidate for the development of enantioselective catalysts, which are essential for the production of enantiomerically pure compounds in various chemical processes.
Used in Synthesis of Biologically Active Molecules:
(R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine is also used as an ingredient in the synthesis of biologically active molecules. Its chiral properties and versatility in controlling stereochemistry make it a valuable component in the development of new drugs and other bioactive compounds with potential therapeutic applications.

InChI:InChI=1/C18H21NO3S/c1-15-7-9-18(10-8-15)23(20,21)22-17-11-12-19(14-17)13-16-5-3-2-4-6-16/h2-10,17H,11-14H2,1H3/t17-/m1/s1

Upstream product

• 1227263-77-5 (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol 
• 6159-55-3 (+)-vasicinol 
• 116183-79-0 (3S)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine 
• 116143-02-3 (3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate 
• 101385-90-4 (S)-N-benzyl-3-hydroxypyrrolidine 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 859213-31-3 (S)-1-benzyl-3-(1-pyrrolidinyl)pyrrolidine 
• 114715-38-7 (3S)-1-benzyl-3-pyrrolidinamine 
• 169749-99-9 (3S)-(-)-1-benzyl-3-(methylamino)pyrrolidine 
• 69478-77-9 ((S)-1-Benzyl-pyrrolidin-3-yl)-dimethyl-amine 
• 114636-29-2 (3S)-3-azido-1-(phenylmethyl)pyrrolidine 

Relevant academic research and scientific papers

Exploring Derivatives of Quinazoline Alkaloid l-Vasicine as Cap Groups in the Design and Biological Mechanistic Evaluation of Novel Antitumor Histone Deacetylase Inhibitors

l-Vasicine is a quinazoline alkaloid with an electron dense ring and additional functionalities in its structure. Employing target oriented synthesis (TOS) based on in silico studies, molecules with significant docking scores containing different derivatives of l-vasicine as caps were synthesized. Interestingly, one molecule, i.e., 4a, which contained 3-hyroxypyrrolidine as a cap group and a six carbon long aliphatic chain as a linker was found to inhibit HDACs. 4a showed more specificity toward class I HDAC isoforms. Also 4a was found to be less cytotoxic toward normal cell lines as compared to cancer cell lines. 4a inhibited cancer cell growth and induced cell death by various mechanisms. However, 4a was found to induce cell death independent of ROS generation, and unlike many natural product based HDAC inhibitors, 4a was found to be nontoxic under in vivo conditions. Importantly, we for the first time report the possibility of using a 3-hydroxypyrrolidine cap for the synthesis of HDAC inhibitors with good potency.

PIPERAZINE AND AMINOPYRROLIDINE COMPOUNDS AS HISTAMINE H3 RECEPTOR ANTAGONISTS

The invention relates to compounds of formula (I) wherein R1 to R3 and X0, X1, X2 have the meaning as cited in the description and the claims. Said compounds are useful as Histamine H3 receptor antago

Fluoronaphthyridines and -quinolines as Antibacterial Agents. 5. Synthesis and Antimicrobial Activity of Chiral 1-tert-Butyl-6-fluoro-7-substituted-naphthyridones

A series of novel 7-substituted-1-tert-butyl-6-fluoronaphthyridone-3-carboxylic acids has been prepared.These derivatives are characterized by chiral aminopyrrolidine substituents at the 7 position.In this paper we report the full details of the asymmetric synthesis of this series of compounds.Structure-activity relationship studies indicate that the absolute stereochemistry at the asymmetric centers of the pyrrolidine ring is critical for maintaining good activity.Compounds 60 and 61 (3-amino-4-methylpyrrolidine enantiomers) were selected for preclinical evaluation.

Benzazepine and benzothiazepine derivatives

Vasodilating activity is exhibited by compounds having the formula STR1 wherein X can be --S--or --CH2 --; and R2 is STR2 depending upon the definition of X.