218933-96-1

Basic information

• Product Name: (2R,2'S)-2-[(2'-(methoxymethyl)pyrrolidin-1'-yl)amino]butyl phenyl sulfone
• Synonyms: (2R,2'S)-2-[(2'-(methoxymethyl)pyrrolidin-1'-yl)amino]butyl phenyl sulfone
• CAS NO: 218933-96-1
• Molecular Weight: 326.46
• Mol File: 218933-96-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,2'S)-2-[(2'-(methoxymethyl)pyrrolidin-1'-yl)amino]butyl phenyl sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,2'S)-2-[(2'-(methoxymethyl)pyrrolidin-1'-yl)amino]butyl phenyl sulfone(218933-96-1)
• EPA Substance Registry System: (2R,2'S)-2-[(2'-(methoxymethyl)pyrrolidin-1'-yl)amino]butyl phenyl sulfone(218933-96-1)

Safety Data

• Hazardous Substances Data: 218933-96-1(Hazardous Substances Data)

Upstream product

• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 
• 74963-80-7 (E)-(but-1-en-1-ylsulfonyl)benzene 

Downstream Products

• 233264-94-3 (R)-2-dibenzylaminobutyl phenyl sulfone 
• 221344-96-3 (R)-2-aminobutyl phenyl sulfone 

Relevant articles and documents

Asymmetric synthesis of α-substituted β-amino sulfones by aza-Michael addition to alkenyl sulfones and subsequent α-alkylation

The aza-Michael addition of enantiopure 1-aminopyrrolidines to (E)- alkenyl sulfones in the presence of a catalytic amount of ytterbium trifluoromethanesulfonate [Yb(OTf)3] yields β-hydrazino sulfones in moderate to good yields and with diastereoselectivities of up to 98%. The latter undergo reductive N-N bond cleavage with BH3 · THF and, after N- protection with Boc2O or benzyl bromide, afford N-protected β-amino sulfones with moderate to high enantiomeric excesses (ee = 42 to ≥96%) without racemization. Subsequent α-alkylation of the N,N-dibenzyl protected β-amino sulfones with various electrophiles yields α-alkyl-β-amino sulfones in excellent yields (88-97%) with high diastereomeric (de ≥96 to ≥98%) and enantiomeric purity (ee = 94 to ≥96%). The absolute configuration of the new stereogenic centre was determined by X-ray structural analysis and confirmed by NMR spectroscopy (NOE experiments). Possible reaction mechanisms for the conjugate addition and α-alkylation are presented.