678965-59-8

Basic information

• Product Name: 2-Aziridinemethanol, 1-[(1R)-1-phenylethyl]-, 4-methylbenzenesulfonate (ester), (2S)-
• CAS NO: 678965-59-8
• Molecular Formula: C18H21NO3S
• Molecular Weight: 331.436
• Mol File: 678965-59-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Aziridinemethanol, 1-[(1R)-1-phenylethyl]-, 4-methylbenzenesulfonate (ester), (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aziridinemethanol, 1-[(1R)-1-phenylethyl]-, 4-methylbenzenesulfonate (ester), (2S)-(678965-59-8)
• EPA Substance Registry System: 2-Aziridinemethanol, 1-[(1R)-1-phenylethyl]-, 4-methylbenzenesulfonate (ester), (2S)-(678965-59-8)

Safety Data

• Hazardous Substances Data: 678965-59-8(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 173143-73-2 N-<(R)-(+)-α-methylbenzyl>aziridine-2(S)-methanol 

Downstream Products

• 1093278-37-5 (2S)-[(2,6-dimethylphenoxy)methyl]-1-[(R)-1-phenylethyl]aziridine 
• 1093278-35-3 (2R)-benzyl-1-[(R)-1-phenylethyl]aziridine 
• 1093278-34-2 (2S)-(azidomethyl)-1-[(R)-1-phenylethyl]aziridine 

Relevant articles and documents

Nucleophilic substitution of (sulfonyloxymethyl)aziridines: an asymmetric synthesis of both isomers of mexiletine

The nucleophilic substitution reactions of 1-[1′(R)-α-methylbenzyl]-(2R)- and (2S)-(sulfonyloxymethyl)aziridines were carried out with various nucleophiles including N3-, MeO-, CN-, SCN-, and diarylcuprates. The reaction pathway is influenced by the stereochemistry of the substrates, nucleophiles, and also the structure of the leaving groups. When the reaction site is less sterically hindered for the reactive nucleophiles to approach to the substrate 1-[1′(R)-α-methylbenzyl]-(2S)-(p-toluenesulfonyloxymethyl)aziridines, product is obtained as a single isomer while all the other starting materials afford a mixture of two isomers from two different reaction pathways. Application of this method enabled us to prepare both isomers of orally effective antiarrhythmic agent mexiletine.

The Mechanism of Nucleophilic Substitution of 1-Alkyl-2-(tosyloxymethyl)- aziridines

The stereochemical course of nucleophilic substitution of 1-alkyl-2-(tosyloxymethyl)aziridines has been elucidated by a study using a chiral substrate, which confirmed that no initial ring opening and subsequent ring closure occurred but that instead direct substitution at the exocyclic methylene function took place. Consequently, these N-alkylaziridines exhibit a totally different reactivity towards nucleophiles as compared to the corresponding activated aziridines with an electron-withdrawing group at nitrogen, which has important stereochemical implications.