801297-21-2

Basic information

• Product Name: Cyclohexaneacetic acid, 2-(aminocarbonyl)-2-[[(1R)-1-phenylethyl]amino]-, ethyl ester, (1R,2S)-
• CAS NO: 801297-21-2
• Molecular Formula: C19H28N2O3
• Molecular Weight: 332.443
• Mol File: 801297-21-2.mol

Chemical Properties

• CAS DataBase Reference: Cyclohexaneacetic acid, 2-(aminocarbonyl)-2-[[(1R)-1-phenylethyl]amino]-, ethyl ester, (1R,2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexaneacetic acid, 2-(aminocarbonyl)-2-[[(1R)-1-phenylethyl]amino]-, ethyl ester, (1R,2S)-(801297-21-2)
• EPA Substance Registry System: Cyclohexaneacetic acid, 2-(aminocarbonyl)-2-[[(1R)-1-phenylethyl]amino]-, ethyl ester, (1R,2S)-(801297-21-2)

Safety Data

• Hazardous Substances Data: 801297-21-2(Hazardous Substances Data)

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 24731-17-7 ethyl 2-(2-oxocyclohexyl)acetate 
• 799781-87-6 ethyl-2-[2(RS)-cyano-(2(RS)-(1(R)-phenylethyl)amino)cyclohex-1(RS)-yl]ethanoate 

Downstream Products

• 799781-94-5 (1S,6R)-1-((1(R)-phenylethyl)amino)-cis-3-azabicyclo[4.4.0]decan-2,4-dione 

Relevant articles and documents

Stereoselective synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3- azabicyclo[4.4.0]decan-2,4-dione hydrochlorides: Bicyclic glutamic acid derivatives

Asymmetric synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3-azabicyclo[4.4. 0]decan-2,4-diones has been achieved. The underlying second generation asymmetric synthesis proceeds via a Strecker reaction with commercially available (R)-1-phenylethylamine (1-PEA) as chiral auxiliary, TMSCN as cyanide source and racemic ethyl 2-(2-oxocyclohex-1-yl)ethanoate. A ring closure addition-elimination reaction between an amide nitrogen and the ester functionality leads to the 1-amino-3-azabicyclo[4.4.0]decan-2,4-diones. The absolute configurations of the title compounds have been assigned based on detailed NMR-spectroscopic analysis and X-ray data. Graphical Abstract.