2,4,4-Trimethyl-N-sulfinyl-2-pentanamine

CAS 2648-42-2, Cat. No EN300-46746494
Reagent for S(VI) transfer

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2,4,4-Trimethyl-N-sulfinyl-2-pentanamine (t-OctNSO) is a bench-stable sulfinylamine reagent that serves as a versatile sulfur(VI) transfer reagent and precursor to unsymmetrical sulfurdiimides¹. In the reported methodology², it is converted into an unsymmetrical sulfurdiimide linchpin, which enables the modular three-component synthesis of sulfondiimidamides through sequential reactions with organometallic reagents, oxidative fluorination, and amine substitution. The reagent supports a broad substrate scope, including aryl, heteroaryl, vinyl, and alkyl organometallics, providing stable sulfondiimidoyl fluoride intermediates that can be transformed into diverse sulfondiimidamides bearing a wide range of medicinally relevant amines. The tert-octyl group acts as a temporary, acid-labile protecting group, remaining stable throughout the synthesis but readily removed with trifluoroacetic acid to generate NH-sulfondiimidamides for further derivatization (e.g., cyanation, amidation, sulfonamidation, and urea formation). The reagent can be used in the iron-catalyzed decarboxylative sulfinylation of alkyl carboxylic acids³. The method is operationally simple and scalable, exhibits broad functional group tolerance, and is translatable to continuous-flow synthesis.

Synonyms: 2,4,4-trimethyl-N-sulfinyl-2-pentanamine; butylamine, 1,1,3,3-tetramethyl-N-sulfinyl-; N-sulfinyl-tert-octylamine; t-OctNSO