143393-98-0

Basic information

• Product Name: Pyrrolo[1,2-a]pyrazin-1(2H)-one, hexahydro-4-methyl-, (4R-cis)- (9CI)
• Synonyms: Pyrrolo[1,2-a]pyrazin-1(2H)-one, hexahydro-4-methyl-, (4R-cis)- (9CI);(4R,8AR)-4-METHYLHEXAHYDROPYRROLO[1,2-A]PYRAZIN-1(2H)-ONE
• CAS NO: 143393-98-0
• Molecular Formula: C8H14N2O
• Molecular Weight: 154.20956
• Product Categories: PIPERIDINE;PYRROLE
• Mol File: 143393-98-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyrrolo[1,2-a]pyrazin-1(2H)-one, hexahydro-4-methyl-, (4R-cis)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolo[1,2-a]pyrazin-1(2H)-one, hexahydro-4-methyl-, (4R-cis)- (9CI)(143393-98-0)
• EPA Substance Registry System: Pyrrolo[1,2-a]pyrazin-1(2H)-one, hexahydro-4-methyl-, (4R-cis)- (9CI)(143393-98-0)

Safety Data

• Hazardous Substances Data: 143393-98-0(Hazardous Substances Data)

Usage

General Description

Pyrrolo[1,2-a]pyrazin-1(2H)-one, hexahydro-4-methyl-, (4R-cis)- (9CI), also known as cis-4-Methylhexahydropyrrolo[1,2-a]pyrazin-1-one, is a chemical compound with a molecular formula of C8H12N2O. It is a heterocyclic compound with a pyrrolopyrazinone core structure and a cis-configuration at the 4-position of the hexahydro-4-methyl group. Pyrrolo[1,2-a]pyrazin-1(2H)-one, hexahydro-4-methyl-, (4R-cis)- (9CI) is used in pharmaceutical research as a building block for the synthesis of various bioactive molecules and pharmaceutical agents due to its unique structural and chemical properties. It may also have potential biological activities that make it an interesting target for further study in the field of medicinal chemistry.

Upstream product

• 114376-47-5 D-N-acetylproline methyl ester 
• 143317-63-9 (R)-1-((E)-1-Methyl-2-nitro-vinyl)-pyrrolidine-2-carboxylic acid methyl ester 

Relevant articles and documents

Lactam & amide acetals XXI. Use of pyroglutamic acid and proline in chiral synthesis of conformationally constrained piperazinones

Making use of amide activation chiral synthesis of (+)-(1S,5R)- and (-)-(1R,5S)-3,8-diazabicyclo [3.2.1]octan-2-ones (1 and 2) has been achieved from L- and D-pyroglutamates, and of (-)-(2R,6S)-, (-)-(2S,6S)-, (+)-(2s,6R)- and (+)-(2R,6R)-2-methyl-1,4-diazabicyclo[4.3.0]nonan-5-ones (3a,3b,4a and 4b) from L & D-proline methyl esters respectively. The key step of the synthesis involves a stereo-selective catalytic hydrogenation, accompanied with spontaneous cyclisation, o the nitroenamines 11, 14, 17 and 19. While this reaction was stereospecific in the case of pyro-Glu derived nitroenamines ( 11 and 14), with N-acetyl-proline derived nitroenamines (17 and 19) both 2R and 2S diastereoisomers were obtained with 40% d.e. of the diastereomer with 2-CH3 oriented cis to the 6-H. The piperazinones 1 and 2 on treatment with methanolic HCl at room temperature yielded the corresponding optically pure 5-aminomethylprolines 12 and 15 respectively.