cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole is used as a pharmaceutical intermediate in the preparation of Bicyclic pyrazole bruton's tyrosine kinase inhibitors and anticancer active ingredients. It is also used in the synthesis of other organics , such as 6-heterocycloalkyl quinazoline derivatives.
General procedure for the synthesis of tert-butyl cis-tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate from tert-butyl cis-5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate: To tert-butyl (5 g, 16.5 mmol)-5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (5 g), 16.5 mmol ) was added to a solution of 10% Pd(OH)2/C catalyst (0.5 g) in methanol (50 mL). The reaction mixture was subjected to a hydrogen atmosphere (60 psi) and stirred at 60 °C overnight and subsequently cooled to room temperature. The reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to afford tert-butyl (3R,6aS)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate as a colorless oil (2.3 g, 66% yield).
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[2] Patent: WO2015/120049, 2015, A1. Location in patent: Page/Page column 139; 140
[3] Patent: WO2016/191172, 2016, A1. Location in patent: Page/Page column 86
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