2-Boc-hexahydro-pyrrolo[3,4-c]pyrrole

Uses

2-Boc-Hexahydro-pyrrolo[3,4-C]pyrrole is an organic synthetic intermediate compound used in the preparation of anticancer agent compounds and sigma-2 ligands.

Synthesis

Example 6C: Synthesis of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate To a solution of tert-butyl 5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (107.8 g, 0.356 mol), the product of Example 6B, in methanol (250 mL) was added wet 20% Pd(OH)2/C catalyst (10.8 g). The reaction mixture was hydrogenated for 2.5 hours at 50°C and 60 psi under a hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford the title compound tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (74 g, 0.35 mol, 98% yield). Mass spectrum (DCI/NH3) m/z: 213 ([M+H]+).

References

[1] Patent: US2005/65178, 2005, A1. Location in patent: Page/Page column 22
[2] Patent: US2005/101602, 2005, A1. Location in patent: Page/Page column 28
[3] Patent: WO2009/111550, 2009, A1. Location in patent: Page/Page column 37
[4] Patent: WO2013/71697, 2013, A1. Location in patent: Paragraph 00250
[5] Patent: US2014/228361, 2014, A1. Location in patent: Paragraph 0371-0372