423123-15-3

Basic information

• Product Name: (R)-2-((S)-2-Methoxymethyl-pyrrolidin-1-ylamino)-propane-1-sulfonic acid cyclohexyl ester
• Synonyms: (R)-2-((S)-2-Methoxymethyl-pyrrolidin-1-ylamino)-propane-1-sulfonic acid cyclohexyl ester
• CAS NO: 423123-15-3
• Molecular Weight: 334.48
• Mol File: 423123-15-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-2-((S)-2-Methoxymethyl-pyrrolidin-1-ylamino)-propane-1-sulfonic acid cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-((S)-2-Methoxymethyl-pyrrolidin-1-ylamino)-propane-1-sulfonic acid cyclohexyl ester(423123-15-3)
• EPA Substance Registry System: (R)-2-((S)-2-Methoxymethyl-pyrrolidin-1-ylamino)-propane-1-sulfonic acid cyclohexyl ester(423123-15-3)

Safety Data

• Hazardous Substances Data: 423123-15-3(Hazardous Substances Data)

Upstream product

• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 

Downstream Products

• 423123-26-6 (R)-2-Amino-propane-1-sulfonic acid cyclohexyl ester 

Relevant articles and documents

Asymmetric synthesis of β-amino cyclohexyl sulfonates, β-sultams and γ-sultones

An efficient asymmetric synthesis of β-aminocyclohexyl sulfonates, β-sultams and γ-sultones has been developed. The key step of the synthesis is the Lewis acid catalyzed aza-Michael addition of the enantiopure hydrazines SAMP [(S)-1] or RAMBO [(R,R,R)-2] to alkenylcyclohexyl sulfonates 3. This leads to β-hydrazino sulfonates 4a-k in moderate to good yields (41-85%) and diastereomeric excesses (de = 44-90%). The epimers were separated by preparative HPLC. Subsequent reductive N-N bond cleavage with BH 3·THF and protection of the resulting amines with CbzCl gave N-Cbz-protected β-aminocyclohexyl sulfonates 6a-k in moderate to good yields (38-68% over 2 steps) and high enantiomeric excesses (ee ≥ 96%). α-Alkylation of 6 with various electrophiles afforded α-alkyl-β -aminocyclohexyl sulfonates 10a-g in good to excellent yields (67-92%) and moderate to high diastereomeric excesses (de = 71-93%). After alkylation with allyl iodide, the first asymmetric iodosultonization was achieved with high selectivities. Compounds 6g-k were also cyclized in a four-step synthesis to highly enantio-enriched 3-substituted-1,2-thiazetidine 1,1-dioxides (β-sultams) 9a-e.