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

Product Name8-BOC-3,8-DIAZA-BICYCLO[3.2.1]OCTANE
CAS149771-44-8
MFC11H20N2O2
MW212.29
EINECS
MOL File149771-44-8.mol

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

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

TERT-BUTYL 3-BENZYL-3,8-DIAZABICYCLO[3.2.1]OCTANE-8-CARBOXYLATE

149771-43-7

149771-44-8

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

Preparation Products And Raw materials

Raw materials

3,8-Diazabicyclo[3.2.1]octane-8-carboxylic acid, 3-(2,2,2-trifluoroacetyl)-, 1,1-diMethylethyl ester TERT-BUTYL 3-BENZYL-3,8-DIAZABICYCLO[3.2.1]OCTANE-8-CARBOXYLATE Ethanol Hydrogen

Preparation Products