1304771-29-6

Basic information

• Product Name: (S)-N-((S)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide
• Synonyms: (S)-N-((S)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide
• CAS NO: 1304771-29-6
• Molecular Weight: 255.381
• Mol File: 1304771-29-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (S)-N-((S)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-((S)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide(1304771-29-6)
• EPA Substance Registry System: (S)-N-((S)-1-(3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide(1304771-29-6)

Safety Data

• Hazardous Substances Data: 1304771-29-6(Hazardous Substances Data)

Upstream product

• 89691-63-4 1-(3-methoxy)-phenylethanol 
• 343338-28-3 (S)-2-methylpropane-2-sulfinamide 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 

Downstream Products

• 50919-07-8 (S)-1-(3-methoxyphenyl)ethylamine 

Relevant articles and documents

Transition-Metal-Free Hydrogen Autotransfer: Diastereoselective N-Alkylation of Amines with Racemic Alcohols

A practical method for the synthesis of α-chiral amines by alkylation of amines with alcohols in the absence of any transition-metal catalysts has been developed. Under the co-catalysis of a ketone and NaOH, racemic secondary alcohols reacted with Ellman's chiral tert-butanesulfinamide by a hydrogen autotransfer process to afford chiral amines with high diastereoselectivities (up to >99:1). Broad substrate scope and up to a 10 gram scale production of chiral amines were demonstrated. The method was applied to the synthesis of chiral deuterium-labelled amines with high deuterium incorporation and optical purity, including examples of chiral deuterated drugs. The configuration of amine products is found to be determined solely by the configuration of the chiral tert-butanesulfinamide regardless of that of alcohols, and this is corroborated by DFT calculations. Further mechanistic studies showed that the reaction is initiated by the ketone catalyst and involves a transition state similar to that proposed for the Meerwein–Ponndorf–Verley (MPV) reduction, and importantly, it is the interaction of the sodium cation of the base with both the nitrogen and oxygen atoms of the sulfinamide moiety that makes feasible, and determines the diastereoselectivity of, the reaction.

Synthesis of highly enantiomerically enriched amines by asymmetric transfer hydrogenation of N-(tert-Butylsulfinyl)imines

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Asymmetric synthesis of chiral primary amines by transfer hydrogenation of N -(tert -Butanesulfinyl)ketimines

(Figure presented) The diastereoselective reduction of (R)-N-(tert- butanesulfinyl)ketimines by a ruthenium-catalyzed asymmetric transfer hydrogenation process in isopropyl alcohol, followed by desulfinylation of the nitrogen atom, is an excellent method to prepare highly enantiomerically enriched α-branched primary amines (up to >99% ee) in short reaction times (1-4 h). (1S,2R)-1-Amino-2-indanol has been shown to be a very efficient ligand to perform this transformation. Ketimines bearing either an aryl or a heteroaryl group and an alkyl group as substituents of the iminic carbon atom are very good substrates for this process. The reduction of a dialkyl ketimine could also be achieved, affording the expected amine with moderate optical purity (69% ee). Some amines which are precursors of very interesting biologically and pharmacologically active compounds have been prepared in excellent yields and enantiomeric excesses.