116183-79-0

Basic information

• Product Name: (S)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine
• Synonyms: (S)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine;[(3S)-1-benzylpyrrolidin-3-yl] 4-methylbenzenesulfonate
• CAS NO: 116183-79-0
• Molecular Formula: C₁₈H₂₁NO₃S
• Molecular Weight: 331.43
• Mol File: 116183-79-0.mol

Chemical Properties

• Melting Point: 68 °C
• Boiling Point: 466.3 °C at 760 mmHg
• Flash Point: 235.8 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 7.15E-09mmHg at 25°C
• Refractive Index: 1.616
• PKA: 7.42±0.40(Predicted)
• CAS DataBase Reference: (S)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine(116183-79-0)
• EPA Substance Registry System: (S)-1-Benzyl-3-[(p-tolylsulfonyl)oxy]pyrrolidine(116183-79-0)

Safety Data

• Hazardous Substances Data: 116183-79-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
(S)-BTPP is employed as a chiral building block for the synthesis of pharmaceuticals and agrochemicals, leveraging its unique structural features and chiral nature to produce optically pure compounds. This ensures the efficacy and safety of the final products, which is critical in the development of new drugs and agrochemicals.
Used in Asymmetric Catalysis:
(S)-BTPP is utilized as a catalyst in asymmetric catalysis, a process that allows for the selective formation of one enantiomer over another. This is particularly important in the synthesis of enantioselective compounds, where the desired biological activity is often associated with a specific enantiomer.
Used in the Development of New Materials and Fine Chemicals:
(S)-BTPP is used as a reagent in the development of new materials and fine chemicals, taking advantage of its unique structural features to create novel compounds with specific properties. This contributes to the advancement of various industries, including materials science, chemical engineering, and specialty chemicals.
Used in the Creation of Biologically Active Molecules:
(S)-BTPP is employed in the synthesis of biologically active molecules, capitalizing on its potential to create compounds with specific biological activities. This is particularly relevant in the discovery and development of new drugs and therapeutic agents, where the ability to produce biologically active molecules is crucial.

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-/m0/s1

Upstream product

• 775-15-5 1-benzyl-3-pyrrolidinol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1227263-77-5 (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol 
• 6159-55-3 (+)-vasicinol 
• 101385-90-4 (S)-N-benzyl-3-hydroxypyrrolidine 
• 122929-12-8 rac-N-benzyl-3-pyrrolidinyl acetate 

Downstream Products

• 144043-17-4 (3R)-1-benzyl-N-methylpyrrolidin-3-amine 
• 116143-02-3 (3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate 
• 114715-39-8 (R)-1-benzyl-3-aminopyrrolidine 
• 1050646-92-8 ((S)-1-Benzylpyrrolidin-3-yl)(3-methoxyphenyl)phenylacetonitrile 
• 197964-14-0 2,2-diphenyl-2-[(3S)-N-benzyl-pyrrolidin-3-yl]acetonitrile 
• 116183-80-3 (3R)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine 
• 114636-29-2 (3S)-3-azido-1-(phenylmethyl)pyrrolidine 
• 169749-99-9 (3S)-(-)-1-benzyl-3-(methylamino)pyrrolidine 
• 69478-77-9 ((S)-1-Benzyl-pyrrolidin-3-yl)-dimethyl-amine 
• 101385-90-4 (R)-N-benzyl-3-hydroxypyrrolidine 
• 69478-77-9 ((R)-1-benzylpyrrolidin-3-yl)dimethylamine 
• 116143-03-4 (3R)-3-azido-1-(phenylmethyl)pyrrolidine 
• 1015443-62-5 (R)-4-(1-benzyl-pyrrolidin-3-yl)-thiomorpholine 1,1-dioxide 

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.

Preparation of enantiomerically pure N-heterocyclic amino alcohols by enzymatic kinetic resolution

Abstract The synthesis of both enantiomers of N-benzyl-3-hydroxypyrrolidine and N-benzyl-3-hydroxypiperidine via enzymatic kinetic resolution of the corresponding racemic esters is described. Various commercially available hydrolases were studied as biocatalysts in native and immobilized form. The best results were obtained with lipases PS, AK, CAL-B and with protease Alcalase, which were active and selective for the kinetic resolutions of racemic esters (E > 100). Under optimized reaction conditions, highly enantiomerically enriched (up to 99.5% ee) resolution products were obtained. Lipase and protease showed opposite enantiopreference on the esters, allowing the preparation of both enantiomers of the target compounds. Semi-continuous reactions in column reactors with immobilized biocatalysts were also performed with high enantioselectivities. Inversion of the configuration at C(3) of N-benzyl-3-hydroxypyrrolidine was quantitatively effected in a short number of steps.

Quaternary ammonium diphenylmethyl compounds useful as muscarinic receptor antagonists

The invention provides compounds of formula I: in salt or zwitterionic form or a pharmaceutically acceptable salt thereof, wherein R1-6, a-e and Q are as defined in the specification. These compounds are muscarinic receptor antagonists. The inv

SERINE HYDROLASE INHIBITORS

Provided herein are benzoxazinone compounds of formula (I) and compositions containing the compounds. The compounds and compositions are useful in the methods of inhibiting the action of serine hydrolase, including neutrophil elastase. In certain embodiments, the compounds and compositions are useful in the prevention, amelioration or treatment of serine hydrolase-mediated diseases.

SUBSTITUTED 4-AMINO-1-BENZYLPIPERIDINE COMPOUNDS

This invention provides 4-amino-1-benzylpiperidine and related compounds and pharmaceutically acceptable salts thereof which are useful as muscarinic receptor antagonists. This invention also provides pharmaceutical compositions containing such compounds; processes and intermediates useful for preparing such compounds; and methods for treating disease conditions mediated by muscarinic receptors, such as overactive bladder, irritable bowel syndrome, asthma and chronic obstructive pulmonary disease, using such compounds.

Diphenylmethyl compounds useful as muscarinic receptor antagonists

This invention provides compounds of formula I: wherein a, b, c, e, m, n, Ar1, R1, R2, R3, R4a, R4b, R5 and R6 are as defined in the specification. The compounds of fo

Crystalline form of a substituted pyrrolidine compound

The invention provides a crystalline naphthalene-1,5-disulfonic acid salt of 2-[(S)-1-(8-methylaminooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide or a solvate thereof. This invention also provides pharmaceutical compositions comprising the salt or prepared

NAPHTHALENE-1,5-DISULFONIC ACID SALTS OF A SUBSTITUTED 4-AMINO-1-(PYRIDYLMETHYL)PIPERIDINE COMPOUND

This invention provides naphthalene-1,5-disulfonic acid salts of 4-{N-[7-(3-(S)-1-carbamoyl-1,1-diphenylmethyl)pyrrolidin-1-yl)hept-1-yl]-N-(isopropyl)amino}-1-(4-methoxypyrid-3-ylmethyl)piperidine, which salts are useful as muscarinic receptor antagonists. This invention is also directed to pharmaceutical compositions comprising these salt forms, methods of using these salt forms for treating medical conditions mediated by muscarinic receptors; and processes for preparing these salt forms.

Diphenylmethyl compounds useful as muscarinic receptor antagonists

This invention provides compounds of formula I: wherein a, b, c, e, m, R1, R2, R3, R4a, R4b, R5, R6, R7 and R8are as defined in the specification. The compo

Substituted pyrrolidine and related compounds

This invention is directed to compounds of formula I: wherein R1-R5 and a-e are as defined in the specification; or pharmaceutically-acceptable salt or solvate or stereoisomer thereof. The invention also directed to pharmaceutical co