1630-33-7

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2S)-2-[N-methyl-N-(4-toluenesulfonyl)amino]-1-phenylpropan-1-ol is used as a nasal decongestant for treating symptoms of colds and allergies. It is incorporated into over-the-counter cold and allergy medications to alleviate nasal congestion by constricting blood vessels in the nasal passages.
Used in Regulatory Measures:
Due to its potential use in the illegal production of drugs, (1R,2S)-2-[N-methyl-N-(4-toluenesulfonyl)amino]-1-phenylpropan-1-ol is a regulated substance in many countries. This regulation aims to prevent its misuse and ensure that it is only used for legitimate medical purposes.

Upstream product

• 299-42-3 ephedrine 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

Chlorination reactions of ephedrines revisited. Stereochemistry and functional groups effect on the reaction mechanisms

The stereochemistry of the chlorination reactions with SOCl2 of free ephedrine and pseudoephedrine and their hydrochlorides, examides and sulfonamides was analyzed. Chlorination of free and hydrochloride erythro isomers occurs with 100% inversion of configuration at C-1 (S(N)2 mechanism). Chlorination of examides and sulfonamides of erythro isomers occurs with retention of the configuration at C-1, (S(N)i mechanism). Chlorination reactions in all three isomers and derivatives hydrochlorides, examides or sulfonamides gave the same ratio of erythro (40%) and three isomers (60%) (S(N)1 mechanism). Treatment of the isomeric mixture of the chlorodeoxyephedrine and chlorodeoxypseudoephedrine hydrochloride in DMSO with HCl changes the isomeric ratio, increasing the erythro isomer content (65%). Using the erythro ethanolamines it is possible to arrive stereoselectively at the erythro chloroamines if the compound is previously tosylated or converted to the amide, or to the three chloroamines if the compound is directly chlorinated with SOCl2.

Access to Optically Pure Benzosultams by Superelectrophilic Activation

Through superacid activation, N-(arenesulfonyl)-aminoalcohols derived from readily available ephedrines or amino acids undergo an intramolecular Friedel-Crafts reaction to afford enantiopure benzosultams bearing two adjacent stereocenters in high yields with fully controlled diastereoselectivity. Low-temperature NMR spectroscopy demonstrated the crucial role played by the conformationally restricted chiral dicationic intermediates.