Synthesis of Methoxyisopropyl (MIP)-Protected (R)-Mandelonitrile and Derivatives in a Flow Reactor

Mariëlle M.E. Delville; Jasper J.F. van Gool; Ivo M. van Wijk; Jan C.M. van Hest; Floris P.J.T. Rutjes

doi:10.1556/jfc-d-12-00008

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Journal of Flow Chemistry

Volume/Issue:: Volume 2: Issue 4

Synthesis of Methoxyisopropyl (MIP)-Protected (R)-Mandelonitrile and Derivatives in a Flow Reactor

Authors:

Mariëlle M.E. Delville

Mariëlle M.E. Delville
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Jasper J.F. van Gool

Jasper J.F. van Gool
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Ivo M. van Wijk

Ivo M. van Wijk
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Jan C.M. van Hest

Jan C.M. van Hest
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Floris P.J.T. Rutjes

Floris P.J.T. Rutjes Radboud University Nijmegen, Institute for Molecules and Materials, Heyendaalseweg 135, 6525, AJ Nijmegen, the Netherlands

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Pages:: 124–128

Online Publication Date:: 13 Dec 2012

Publication Date:: 13 Dec 2012

Article Category:: Research Article

DOI:: https://doi.org/10.1556/jfc-d-12-00008

Keywords:: mandelonitrile; flow chemistry; reaction optimization; microreactor; MIP-protection

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Abstract

Cyanohydrins are synthetically versatile chiral building blocks in organic synthesis. They can be conveniently synthesized in enantiomerically pure form via chemoenzymatic hydrogen cyanide addition onto the corresponding aldehyde using hydroxynitrile lyase. Recently, we reported that such transformations can be efficiently carried out in a continuous flow manner using microreactors. Since racemization of enantiopure cyanohydrins occurs readily under slightly basic conditions, they should be protected before the follow-up reactions, preferably under acidic conditions. In this contribution, we demonstrate that the methoxyisopropyl protection of mandelonitrile can be conveniently optimized in an automated microscale continuous flow system and subsequently scaled up under the same conditions by applying a larger flow reactor.

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Journal of Flow Chemistry A Journal of the Flow Chemistry Society

Print ISSN:: 2062-249X

Online ISSN:: 2063-0212

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Journal of Flow Chemistry
Language	English
Size	A4
Year of Foundation	2011
Volumes per Year	1
Issues per Year	4
Founder	Áramlásos Kémiai Tudományos Társaság
Founder's Address	H-1031 Budapest, Hungary Záhony utca 7.
Publisher	Akadémiai Kiadó Springer Nature Switzerland AG
Publisher's Address	H-1117 Budapest, Hungary 1516 Budapest, PO Box 245. CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible Publisher	Chief Executive Officer, Akadémiai Kiadó
ISSN	2062-249X (Print)
ISSN	2063-0212 (Online)