116183-80-3

Basic information

• Product Name: (R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine
• Synonyms: (R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine
• CAS NO: 116183-80-3
• Molecular Formula: C₁₈H₂₁NO₃S
• Molecular Weight: 331.43
• Mol File: 116183-80-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 62 °C
• Boiling Point: 466.319°C at 760 mmHg
• Flash Point: 235.821°C
• Appearance: /
• Density: 1.265g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.617
• PKA: 7.42±0.40(Predicted)
• CAS DataBase Reference: (R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine(116183-80-3)
• EPA Substance Registry System: (R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine(116183-80-3)

Safety Data

• Hazardous Substances Data: 116183-80-3(Hazardous Substances Data)

Usage

General Description

(R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine is a chemical compound with the molecular formula C21H23NO3S. It is a pyrrolidine derivative that contains a benzyl group and a p-tolylsulfonyl oxy moiety. (R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine is often used as a chiral auxiliary in asymmetric synthesis, particularly in the preparation of chiral amino acids and other pharmaceutical intermediates. It serves as a versatile building block in organic synthesis due to its ability to control the stereochemistry of various reactions. Additionally, (R)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine has potential applications as a ligand in catalysis and as an ingredient in the synthesis of biologically active molecules.

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 articles and documents

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.

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.