8-Boc-3,8-diaza-bicyclo[3.2.1]octane

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