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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2011
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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. |
format | Online Article Text |
id | pubmed-3170198 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
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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