Kilogram synthesis of (R)-(-)-denopamine by Ir/f-amphox catalyzed asymmetric hydrogenation

A practical and efficient two-step synthetic process for the preparation of (R)-(-)-denopamine has been developed. The key step asymmetric hydrogenation was conducted at mild temperature (60 °C) under a hydrogen pressure of 50 atm by using Ir/f-amphox as catalyst at low catalyst loading (S/C = 2...

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Autores principales:	Yongpeng Zheng, Xumu Zhang, Runtong Zhang, Baode Ma
Formato:	article
Lenguaje:	EN
Publicado:	KeAi Communications Co. Ltd. 2021
Materias:	(R)-Denopamine Asymmetric hydrogenation f-Amphox Practical process Chemical technology TP1-1185 Biochemistry QD415-436
Acceso en línea:	https://doaj.org/article/19ed00e7bde540b28648ba550eba3ae8
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spelling	oai:doaj.org-article:19ed00e7bde540b28648ba550eba3ae82021-12-02T05:03:57ZKilogram synthesis of (R)-(-)-denopamine by Ir/f-amphox catalyzed asymmetric hydrogenation2666-554910.1016/j.gresc.2021.09.002https://doaj.org/article/19ed00e7bde540b28648ba550eba3ae82021-11-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S2666554921000806https://doaj.org/toc/2666-5549A practical and efficient two-step synthetic process for the preparation of (R)-(-)-denopamine has been developed. The key step asymmetric hydrogenation was conducted at mild temperature (60 °C) under a hydrogen pressure of 50 atm by using Ir/f-amphox as catalyst at low catalyst loading (S/C = 20 000). Under the optimized condition, the desired product (R)-(-)-denopamine was obtained with 70% total yield and > 99.9% ee after crystallization. The pilot-scale experiment has been performed at 500 g level, showing great potential for the production of high quality active pharmaceutical ingredient (API).Yongpeng ZhengXumu ZhangRuntong ZhangBaode MaKeAi Communications Co. Ltd.article(R)-DenopamineAsymmetric hydrogenationf-AmphoxPractical processChemical technologyTP1-1185BiochemistryQD415-436ENGreen Synthesis and Catalysis, Vol 2, Iss 4, Pp 393-396 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	(R)-Denopamine Asymmetric hydrogenation f-Amphox Practical process Chemical technology TP1-1185 Biochemistry QD415-436
spellingShingle	(R)-Denopamine Asymmetric hydrogenation f-Amphox Practical process Chemical technology TP1-1185 Biochemistry QD415-436 Yongpeng Zheng Xumu Zhang Runtong Zhang Baode Ma Kilogram synthesis of (R)-(-)-denopamine by Ir/f-amphox catalyzed asymmetric hydrogenation
description	A practical and efficient two-step synthetic process for the preparation of (R)-(-)-denopamine has been developed. The key step asymmetric hydrogenation was conducted at mild temperature (60 °C) under a hydrogen pressure of 50 atm by using Ir/f-amphox as catalyst at low catalyst loading (S/C = 20 000). Under the optimized condition, the desired product (R)-(-)-denopamine was obtained with 70% total yield and > 99.9% ee after crystallization. The pilot-scale experiment has been performed at 500 g level, showing great potential for the production of high quality active pharmaceutical ingredient (API).
format	article
author	Yongpeng Zheng Xumu Zhang Runtong Zhang Baode Ma
author_facet	Yongpeng Zheng Xumu Zhang Runtong Zhang Baode Ma
author_sort	Yongpeng Zheng
title	Kilogram synthesis of (R)-(-)-denopamine by Ir/f-amphox catalyzed asymmetric hydrogenation
title_short	Kilogram synthesis of (R)-(-)-denopamine by Ir/f-amphox catalyzed asymmetric hydrogenation
title_full	Kilogram synthesis of (R)-(-)-denopamine by Ir/f-amphox catalyzed asymmetric hydrogenation
title_fullStr	Kilogram synthesis of (R)-(-)-denopamine by Ir/f-amphox catalyzed asymmetric hydrogenation
title_full_unstemmed	Kilogram synthesis of (R)-(-)-denopamine by Ir/f-amphox catalyzed asymmetric hydrogenation
title_sort	kilogram synthesis of (r)-(-)-denopamine by ir/f-amphox catalyzed asymmetric hydrogenation
publisher	KeAi Communications Co. Ltd.
publishDate	2021
url	https://doaj.org/article/19ed00e7bde540b28648ba550eba3ae8
work_keys_str_mv	AT yongpengzheng kilogramsynthesisofrdenopaminebyirfamphoxcatalyzedasymmetrichydrogenation AT xumuzhang kilogramsynthesisofrdenopaminebyirfamphoxcatalyzedasymmetrichydrogenation AT runtongzhang kilogramsynthesisofrdenopaminebyirfamphoxcatalyzedasymmetrichydrogenation AT baodema kilogramsynthesisofrdenopaminebyirfamphoxcatalyzedasymmetrichydrogenation
_version_	1718400635270856704

Kilogram synthesis of (R)-(-)-denopamine by Ir/f-amphox catalyzed asymmetric hydrogenation

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