92198-73-7

Basic information

• Product Name: (1-tosylpyrrolidine-2,5-diyl)dimethanol
• Synonyms: (1-tosylpyrrolidine-2,5-diyl)dimethanol;1-[(4-methylphenyl)sulfonyl]-2,5-Pyrrolidine dimethanol
• CAS NO: 92198-73-7
• Molecular Formula: C₁₃H₁₉NO₄S
• Molecular Weight: 285.36
• Mol File: 92198-73-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 475.9±51.0 °C(Predicted)
• Appearance: /
• Density: 1.294±0.06 g/cm3(Predicted)
• PKA: 14.47±0.10(Predicted)
• CAS DataBase Reference: (1-tosylpyrrolidine-2,5-diyl)dimethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1-tosylpyrrolidine-2,5-diyl)dimethanol(92198-73-7)
• EPA Substance Registry System: (1-tosylpyrrolidine-2,5-diyl)dimethanol(92198-73-7)

Safety Data

• Hazardous Substances Data: 92198-73-7(Hazardous Substances Data)

Usage

General Description

(1-Tosylpyrrolidine-2,5-diyl)dimethanol is a chemical compound with the molecular formula C18H23NO3S. It is a tosylate derivative of pyrrolidine-dimethanol, which is commonly used in organic synthesis and as a reagent in chemical reactions. The compound is insoluble in water but soluble in organic solvents such as acetone and methanol. It is also known to be a mild irritant to the skin and eyes, and is commonly handled with appropriate safety precautions in laboratory settings. The compound has been used in the production of pharmaceuticals, dyes, and other industrial applications.

Upstream product

• 145472-49-7 [(S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol 
• 132974-84-6 (-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosylpyrrolidin-2-one 
• 143264-72-6 N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-hydroxypyrrolidine 
• 145472-48-6 (S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde 
• 145472-47-5 (2S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbonitrile 

Downstream Products

• 145472-51-1 (2S,5S)-2,5-Bis-methoxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine 
• 145472-51-1 (2R,5S)-2,5-Bis-methoxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine 

Relevant articles and documents

Synthesis and Further Reactivity of Functionalized Lactam-Derived Enol Triflates

Pyrrolidinone- and piperidinone-derived enol triflates 2 were prepared in high yield (60-97%) from the corresponding lactams 1 using KHMDS and N-(5-chloro-2-pyridyl)triflimide. A structure-stability study on the less stable pyrrolidinone-derived triflates revealed that an N-tosyl group is essential, and an α-ethoxy substituent enhances thermal stability. Substituents at the 3- and 4-position are tolerated. Substitution of the triflate moiety by a wide variety of functional groups was achieved under mild conditions via metal-mediated reactions. Although cuprate couplings proceeded in only moderate yields, several palladium-catalyzed reactions gave good yields of interesting molecules for further synthetic operations (for example, Stille coupling with vinylstannanes, cross-coupling with arylzincs, and carbonylation processes). Preparation of the first enantiopure lactam-derived enol triflate 15 (from (S)-pyroglutamic acid) is described. Enamide hydrogenation of derivative 17 allowed the synthesis of a proline analogue 18 in excellent yield and diastereoselectivity (86% de). ? Abstract published in Advance ACS Abstracts, October 15, 1997.