131912-34-0

Basic information

• Product Name: 1-Tosyl-3-pyrrolidinol Tosylate
• Synonyms: 1-Tosyl-3-pyrrolidinol Tosylate;1-[(4-Methylphenyl)sulfonyl]-3-pyrrolidinol 3-(4-Methylbenzenesulfonate);1-Tosyl-3-tosyloxypyrrolidine
• CAS NO: 131912-34-0
• Molecular Formula: C₁₈H₂₁NO₅S₂
• Molecular Weight: 413.50832
• Product Categories: Aromatics;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 131912-34-0.mol

Chemical Properties

• Boiling Point: 565.6°C at 760 mmHg
• Flash Point: 295.9°C
• Appearance: /
• Density: 1.4g/cm³
• Vapor Pressure: 8.17E-13mmHg at 25°C
• Refractive Index: 1.634
• Solubility: Acetone, Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 1-Tosyl-3-pyrrolidinol Tosylate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Tosyl-3-pyrrolidinol Tosylate(131912-34-0)
• EPA Substance Registry System: 1-Tosyl-3-pyrrolidinol Tosylate(131912-34-0)

Safety Data

• Hazardous Substances Data: 131912-34-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-Tosyl-3-pyrrolidinol Tosylate is used as a synthetic building block for the creation of more complex organic molecules. Its application in organic synthesis is due to its reactivity and ability to form new chemical bonds, which can be further manipulated to produce a wide range of compounds with diverse properties and applications.
Used in Pharmaceutical Industry:
1-Tosyl-3-pyrrolidinol Tosylate is used as an intermediate in the synthesis of pharmaceutical compounds. Its role in this industry is to facilitate the production of drugs with specific therapeutic properties, such as those targeting various diseases and medical conditions.
Used in Chemical Research:
1-Tosyl-3-pyrrolidinol Tosylate is also employed as a research tool in the field of chemistry. It is used to study the mechanisms of various chemical reactions and to gain insights into the behavior of different molecular structures. This knowledge can then be applied to develop new synthetic methods and improve existing ones.

InChI:InChI=1/C18H21NO5S2/c1-14-3-7-17(8-4-14)25(20,21)19-12-11-16(13-19)24-26(22,23)18-9-5-15(2)6-10-18/h3-10,16H,11-13H2,1-2H3

Upstream product

• 40499-83-0 pyrrolidin-3-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 80-48-8 methyl p-toluene sulfonate 
• 170456-83-4 1-tosyl-3-(R)-(-)-hydroxypyrrolidine 
• 1972-28-7 diethylazodicarboxylate 
• 111810-68-5 3-hydroxypyrrolidine hydrochloride 

Downstream Products

• 131912-07-7 α,α-bis(4-fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-3-pyrrolidineacetonitrile 
• 1025728-47-5 1-(4-toluenesulfonyl)-pyrrolidine-3-carbonitrile 

Relevant articles and documents

Copper-Catalyzed Reductive Cross-Coupling of Nonactivated Alkyl Tosylates and Mesylates with Alkyl and Aryl Bromides

A copper-catalyzed reductive cross-coupling reaction of nonactivated alkyl tosylates and mesylates with alkyl and aryl bromides was developed. It provides a practical method for efficient and cost-effective construction of aryl-alkyl and alkyl-alkyl C=C bonds with stereocontrol from readily available substrates. When used in an intramolecular fashion, the reaction enables convenient access to various substituted carbo- or heterocycles, such as 2,3-dihydrobenzofuran and benzochromene derivatives.

Nitrilase-catalyzed enantioselective synthesis of pyrrolidine- And piperidinecarboxylic acids

The enantioselective synthesis of the nonproteinogenic amino acids β-proline and nipecotic acids from their readily available nitriles is achieved in high enantiomeric excess by commercially available nitrilases. The presented procedure comprises not more than 4 steps, thus considerably reducing the multiple steps generally required. Amide formation is also observed for specific heterocyclic nitriles.

MUSCARINIC RECEPTOR ANTAGONISTS

A series of novel 3-phenyl-3-[1-(cyclicalkyl)pyrrolidin-3-yl] glutarimide derivatives have been prepared, including their pharmaceutically acceptable salts. The cyclic moiety present in these compounds is derived from either benzene or a heteroaryl such as benzofuran or 2,3-dihydrobenzofuran, or it is derived from an aromatic heterocyclic such as pyridine, pyrazine or thiophene, and it is attached to the adjacent alkyl group of the molecule by means of one of the available ring carbon atoms situated in the aromatic ring of the aforementioned cyclic ring moiety. These particular compounds are useful in therapy as selective muscarinic receptor antagonists, which are selective for smooth muscle muscarinic sites over cardiac muscarinic sites and therefore, are of value in the treatment of diseases associated with altered motility and/or smooth muscle tone as found in the gut, trachea and bladder. Methods for preparing these compounds from known starting materials are provided.

Muscarinic receptor antagonists

Muscarinic receptor antagonists of formula (I), and their pharmaceutically acceptable salts, wherein Y is --CH 2 --, --(CH 2) 2 --, --CH 2 O--, --(CH 2) 2 O-- or --CH 2 S--; R is --CH or --CONH 2 ; and R 1 is a group of formula (a), where R 2 and R 3 are each independently H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --(CH 2) n OH, halo, trifluoromethyl, cyano, --(CH 2) n NR 4 R 5, --CO(C 1 -C 4 alkyl), --OCO(C 1 -C 4 alkyl), --CH(OH)(C 1 -C 4 alkyl), --C(OH)(C 1 -C 4 alkyl 2, --SO 2 NH 2, --(CH 2) n CONR 6 R 7 or --(CH 2) n COO(C 1 -C 4 alkyl); R 4 is H or C 1 -C 4 alkyl; R 5 is H, C 1 -C 4 alkyl or C 1 -C 4 alkysulphonyl; R 6 and R 7 are each independently H or C 1 -C 4 alkyl; and n is 0, 1 or 2. The compounds are particularly useful in treating irritable bowel syndrome.

PYRROLIDINE DERIVATIVES

Compounds of the formula STR1 wherein R, Y and R 1 are as defined in the specification. These compounds are muscarinic receptor antagonists which are selective for smooth muscle muscarinic sites over cardiac muscarinic sites, and are useful in the treatment of diseases associated with altered motility on tone of smooth muscle, including irritable bowel syndrome, diverticular disease, urinary incontinence, oesophageal achalasia and chronic obstructive airways disease.

Synthesis, Calcium-Channel-Blocking Activity, and Antihypertensive Activity of 4-(Diarylmethyl)-1-piperidines and Structurally Related

A series of 4-(diarylmethyl)-1-piperidines and structurally related compounds were synthesized as calcium-channel blockers and antihypertensive agents.Compounds were evaluated for calcium-channel-blocking activity by determineng their ability to antagonize calcium-induced contractions of isolated rabbit aortic strips.The most potent compounds were those with fluoro substituents in the 3- and/or 4-positions of both rings of the diphenylmethyl group.Bis(4-fluorophenyl)acetonitrile analogue 79 was similar in potency to bis(4-fluorophenyl)methyl compound 1.The methylene analogue of 1 (78) and derivatives of 1 that contained a hydroxyl (76), carbamoyl (80), amino (81), or acetamido (82) substituent on the methyl group were less potent.In most cases substituents on the phenoxy ring, changes in the distance between the aryloxy group and the piperidine nitrogen, and the substitution of S, N(CH3), or CH2 for the oxygen atom of the aryloxy group had only a small to moderate effect on the potency.The best compounds in this series were more potent than verapamil, diltiazem, flunarizine, and lidoflazine, but were less potent than nifedipine.Compounds were evaluated for antihypertensive activity in spontaneusly hypertensive rats (SHR) at an oral dose of 30 mg/kg.Of the 55 compounds tested, only nine produced a statistically significant (p-1-piperidinyl>propoxy>-3-methoxyphenyl>ethanone (63), which produced a 35percent reduction in blood pressure and was similar in activity to nifedipine.At lower doses, however, 4--1-piperidine (93) was one of the most effective antihypertensive agents, producing reductions in blood pressure of 17 and 11percent at oral doses of 10 and 3 mg/kg, respectively; 63 was inactive at 10 mg/kg.