(S,S)-2,8-Diazabicyclo[4,3,0]nonane Chemical Properties

Boiling point:

198.5±8.0 °C(Predicted)

Density 

0.950±0.06 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Methanol (Slightly), Water

pka

11.11±0.20(Predicted)

form 

Oil

color 

Colourless to Yellow

InChI

InChI=1S/C7H14N2/c1-2-6-4-8-5-7(6)9-3-1/h6-9H,1-5H2/t6-,7+/m1/s1

InChIKey

KSCPLKVBWDOSAI-RQJHMYQMSA-N

SMILES

[C@]12([H])CNC[C@@]1([H])CCCN2

CAS DataBase Reference

151213-42-2(CAS DataBase Reference)

Safety Information

HS Code 

29333990

(S,S)-2,8-Diazabicyclo[4,3,0]nonane Usage And Synthesis

Chemical Properties

Clear light red liquid

Uses

(1R,6R)-2,8-Diazabicyclo[4.3.0]nonane is a chiral reagent used in the synthesis of pyrrolopyrimidine derivatives as dual DNA gyrase B and topoisomerase IV inhibitors and potential antibacterial agents.

Synthesis

The general procedure for the synthesis of (4aR,7aR)-octahydro-6-(phenylmethyl)-1H-pyrrolo[3,4-b]pyridine from (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b]pyridine is as follows: 19.4 g (0.09 mol) of (R,R)-8-benzyl-2,8-diazabicyclo[4.3.0]nonane was dissolved in methanol with the addition of 3.96 g of 5% palladium/activated carbon catalyst and hydrogenated at 90 °C and 130 °C for 5 hours. Upon completion of the reaction, the catalyst was removed by filtration and the catalyst was washed with methanol. The filtrate was concentrated under vacuum and the residue was directly distilled without fractionation. A final product of 9.61 g was obtained in 85% yield of the theoretical value. The boiling point of the product was 45-58°C/0.08 mbar.

References

[1] Patent: WO2003/106450, 2003, A1. Location in patent: Page column 58
[2] Patent: US5468742, 1995, A
[3] Patent: US5480879, 1996, A
[4] Oriental Journal of Chemistry, 2013, vol. 29, # 1, p. 241 - 246

(S,S)-2,8-Diazabicyclo[4,3,0]nonane(151213-42-2)Related Product Information

• 3-Ethyl-6,7,8,9-tetrahydro-9-hydroxy-2-Methyl-4H-pyrido[1,2-a]pyriMidin-4-one
• 3-pentylisoindolin-1-one
• Acotiamide INT
• (4aS,7aS)-1-methyloctahydro-1H-pyrrolo[3,4-b]pyridine
• 3-ethyl-9-hydroxy-2-Methyl-4H-pyrido[1,2-a]pyriMidin-4-one
• 3-(2-Chloroethyl)-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one (Paliperidone)
• Indene
• 7-Aminocephalosporanic acid
• 6-Aminopenicillanic acid
• Ribostamycin sulfate
• DBU
• N-NONANE
• CIS-OCTAHYDROPYRROLO[3,4-B]PYRIDINE
• 9-methyl-3,9-diazedicyclo(4,2,1)nonane
• (S,S)-2,8-Diazabicyclo[4,3,0]nonane
• Moxifloxacin Methyl Ester
• 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-hydroxy-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester
• 3-Quinolinecarboxylic acid, 7-[(4aS,7aS)-1-(2-carboxyethyl)octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-