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Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride

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...

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Autores principales: Kozhushkov, Sergei I, Khlebnikov, Alexander F, Kostikov, Rafael R, Yufit, Dmitrii S, de Meijere, Armin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3170198/
https://www.ncbi.nlm.nih.gov/pubmed/21915200
http://dx.doi.org/10.3762/bjoc.7.113
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author Kozhushkov, Sergei I
Khlebnikov, Alexander F
Kostikov, Rafael R
Yufit, Dmitrii S
de Meijere, Armin
author_facet Kozhushkov, Sergei I
Khlebnikov, Alexander F
Kostikov, Rafael R
Yufit, Dmitrii S
de Meijere, Armin
author_sort Kozhushkov, Sergei I
collection PubMed
description 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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spelling pubmed-31701982011-09-13 Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride Kozhushkov, Sergei I Khlebnikov, Alexander F Kostikov, Rafael R Yufit, Dmitrii S de Meijere, Armin Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2011-07-21 /pmc/articles/PMC3170198/ /pubmed/21915200 http://dx.doi.org/10.3762/bjoc.7.113 Text en Copyright © 2011, Kozhushkov et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Kozhushkov, Sergei I
Khlebnikov, Alexander F
Kostikov, Rafael R
Yufit, Dmitrii S
de Meijere, Armin
Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride
title Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride
title_full Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride
title_fullStr Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride
title_full_unstemmed Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride
title_short Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride
title_sort scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3170198/
https://www.ncbi.nlm.nih.gov/pubmed/21915200
http://dx.doi.org/10.3762/bjoc.7.113
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