8-BOC-3,8-DIAZA-BICYCLO[3.2.1]OCTANE Chemical Properties

Boiling point:

295.4±15.0 °C(Predicted)

Density 

1.076±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

9.53±0.20(Predicted)

form 

solid

color 

White to off-white

InChI

InChI=1S/C11H20N2O2/c1-11(2,3)15-10(14)13-8-4-5-9(13)7-12-6-8/h8-9,12H,4-7H2,1-3H3

InChIKey

HNINFCBLGHCFOJ-UHFFFAOYSA-N

SMILES

C12N(C(OC(C)(C)C)=O)C(CC1)CNC2

Safety Information

HS Code 

2933599590

8-BOC-3,8-DIAZA-BICYCLO[3.2.1]OCTANE Usage And Synthesis

Uses

tert-Butyl 3,8-Diazabicyclo[3.2.1]octane-8-carboxylate is used in preparation of isoquinolinone derivatives and pharmaceutical compounds thereof for prevention or treatment of poly(ADP-ribose)polymerase-1 (PARP-1)-associated diseases.

Synthesis

The hydrogenation reaction of tert-butyl 3-benzyl-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (13.0 g, 43.0 mmol) was carried out in ethanol (100 mL, 99%) in the presence of palladium carbon (4.0 g, 5%) catalyst. Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was dried and the solvent evaporated to afford the white powdery product tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate. The yield was 8.4 g (92% yield) and the melting point was 103.4-106°C. The product was obtained as follows.

References

[1] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 674 - 681
[2] Patent: US2002/128271, 2002, A1
[3] Patent: EP1213289, 2002, A1. Location in patent: Page 13
[4] Patent: WO2006/106090, 2006, A1. Location in patent: Page/Page column 16
[5] Tetrahedron Letters, 2002, vol. 43, # 5, p. 899 - 902

8-BOC-3,8-DIAZA-BICYCLO[3.2.1]OCTANE(149771-44-8)Related Product Information

• tert-butyl 4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate
• tert-butyl 6-hydroxy-3-azabicyclo[3.1.0]hexane-3-carboxylate
• 3-AMINO-1-[(1,1-DIMETHYLETHOXY)CARBONYL]-3-PIPERIDINEACETIC ACID METHYL ESTER
• tert-butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate
• tert-Butyl carbazate
• tert-butyl 3,3a,4,5-tetrahydro-5-oxocyclopenta[c]pyrrole-2(1H)-carboxylate
• tert-Butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate hydrochloride
• 2-OXO-2,5-DIHYDRO-PYRROLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• TERT-BUTYL 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE
• tert-butyl 2-oxo-6-azaspiro[3.5]nonane-6-carboxylate
• 1-Oxa-7-azaspiro[4.5]decane-7-carboxylic acid, 3-oxo-, 1,1-diMethylethyl ester
• TERT-BUTYL N-ALLYLCARBAMATE
• 1-Boc-3-methyl-3-hydroxyp...
• 4-Acetyl-piperidine-1-carboxylic acid tert-butyl ester
• N-BOC-3-METHYLENE-PIPERIDINE
• (R)-1-N-Boc-2-methylpiperazine
• (R)-2-(Aminomethyl)-1-N-Boc-pyyrolidine
• (S)-1-N-Boc-2-(aminomethyl)pyrrolidine