143393-96-8

Basic information

• Product Name: 3,8-Diazabicyclo[3.2.1]octan-2-one,(1S)-(9CI)
• Synonyms: 3,8-Diazabicyclo[3.2.1]octan-2-one,(1S)-(9CI);(1S,5R)-3,8-Diazabicyclo[3.2.1]octan-2-one;(1S)-3,8-Diazabicyclo[3.2.1]octan-2-one
• CAS NO: 143393-96-8
• Molecular Formula: C6H10N2O
• Molecular Weight: 126.16
• Product Categories: PIPERAZINE
• Mol File: 143393-96-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,8-Diazabicyclo[3.2.1]octan-2-one,(1S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,8-Diazabicyclo[3.2.1]octan-2-one,(1S)-(9CI)(143393-96-8)
• EPA Substance Registry System: 3,8-Diazabicyclo[3.2.1]octan-2-one,(1S)-(9CI)(143393-96-8)

Safety Data

• Hazardous Substances Data: 143393-96-8(Hazardous Substances Data)

Upstream product

• 38854-94-3 N-benzyl-L-pyroglutamic acid 
• 130516-24-4 (S)-(+)-1-Benzyl-5-thioxoproline methyl ester 
• 103301-78-6 methyl (2S)-1-benzyl-5-pyrrolidone-2-carboxylate 
• 143317-65-1 (S)-(+)-1-Benzyl-2-thiomethoxy-5-methoxycarbonyl-1-pyrrolinium iodide 
• 143317-57-1 (S)-(+)-1-Benzyl-5-nitromethyleneproline 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.