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Kozhushkov SI, Khlebnikov AF, Kostikov RR, et al. Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride. Beilstein J Org Chem. 2011;7:1003-6doi: 10.3762/bjoc.7.113.
Kozhushkov, S. I., Khlebnikov, A. F., Kostikov, R. R., Yufit, D. S., & de Meijere, A. (2011). Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride. Beilstein journal of organic chemistry, 71003-6. https://doi.org/10.3762/bjoc.7.113
Kozhushkov, Sergei I, et al. "Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride." Beilstein journal of organic chemistry vol. 7 (2011): 1003-6. doi: https://doi.org/10.3762/bjoc.7.113
Kozhushkov SI, Khlebnikov AF, Kostikov RR, Yufit DS, de Meijere A. Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride. Beilstein J Org Chem. 2011;7:1003-6. doi: 10.3762/bjoc.7.113. Epub 2011 Jul 21. PMID: 21915200; PMCID: PMC3170198.
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Beilstein J Org Chem. 2011;7:1003-6. doi: 10.3762/bjoc.7.113. Epub 2011 Jul 21.

Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride.

Beilstein journal of organic chemistry

Sergei I Kozhushkov, Alexander F Khlebnikov, Rafael R Kostikov, Dmitrii S Yufit, Armin de Meijere

Affiliations

  1. Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany.

PMID: 21915200 PMCID: PMC3170198 DOI: 10.3762/bjoc.7.113

Abstract

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.

Keywords: Curtius degradation; amines; building blocks; carboxylic acids; cyclopropanes

References

  1. Chem Commun (Camb). 2001 Sep 21;(18):1792-3 - PubMed
  2. J Org Chem. 2010 Dec 17;75(24):8351-4 - PubMed

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