Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride

Autor: Sergei I. Kozhushkov, Alexander F. Khlebnikov, Rafael R. Kostikov, Dmitrii S. Yufit, Armin de Meijere
Jazyk: angličtina
Rok vydání: 2011
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 7, Iss 1, Pp 1003-1006 (2011)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.7.113
Popis: 1-Cyclopropylcyclopropanecarboxylic acid (2), which is accessible on a large scale (900 mmol) from 1-bromo-1-cyclopropylcyclopropane (1) in 64% yield (89% on a 12.4 mmol scale), has been subjected to a Curtius degradation employing the Weinstock protocol to furnish the N-Boc-protected (1-cyclopropyl)cyclopropylamine 3 (76%). Deprotection of 3 with hydrogen chloride in diethyl ether gave the (1-cyclopropyl)cyclopropylamine hydrochloride (4·HCl) in 87% yield.
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