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Four Step Total Synthesis of an H[subscript 3] Receptor Antagonist Using Only Tools Found in a Typical Teaching Laboratory

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Title: Four Step Total Synthesis of an H[subscript 3] Receptor Antagonist Using Only Tools Found in a Typical Teaching Laboratory
Language: English
Authors: Smith, Catherine J. (ORCID 0000-0002-2380-3119), Mansfield, Steven J., Anderson, Edward A. (ORCID 0000-0002-4149-0494), Burton, Jonathan W.
Source: Journal of Chemical Education. Jan 2019 96(1):137-142.
Availability: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Peer Reviewed: Y
Page Count: 6
Publication Date: 2019
Document Type: Journal Articles
Reports - Descriptive
Education Level: Higher Education
Postsecondary Education
High Schools
Secondary Education
Descriptors: Science Instruction, Laboratory Experiments, Universities, Foreign Countries, Organic Chemistry, High School Students, Problem Solving, Teaching Methods, Introductory Courses
Geographic Terms: United Kingdom (England)
DOI: 10.1021/acs.jchemed.7b00982
ISSN: 0021-9584
Abstract: Organic synthesis in a modern research laboratory uses state-of-the-art equipment to provide inert atmospheres, track reaction progress, and facilitate the purification of intermediates. Such facilities are not available in a high school laboratory. In this paper, synthetic organic chemistry is taken back to basics: A four step total synthesis of a potential histamine H[subscript 3] receptor antagonist is completed by A-level students in a school laboratory using only basic equipment. In addition to its bioactivity, the target molecule was selected on the basis of its potentially crystalline nature, allowing for the purification of intermediates by recrystallization. A synthetic route was developed that could be conducted without the need for inert conditions and with intermediates stable enough to be left from one week to the next, with characterization of intermediates and the target compound carried out by collaboration with researchers and analytical facilities at the University of Oxford (U.K.). By working on the project, students not only developed their practical chemistry and problem solving skills, but also experienced the thrill of discovery that inspires people to be scientists.
Abstractor: As Provided
Entry Date: 2019
Accession Number: EJ1202208
Database: ERIC
FullText Text:
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  Data: <searchLink fieldCode="AR" term="%22Smith%2C+Catherine+J%2E%22">Smith, Catherine J.</searchLink> (ORCID <externalLink term="http://orcid.org/0000-0002-2380-3119">0000-0002-2380-3119</externalLink>)<br /><searchLink fieldCode="AR" term="%22Mansfield%2C+Steven+J%2E%22">Mansfield, Steven J.</searchLink><br /><searchLink fieldCode="AR" term="%22Anderson%2C+Edward+A%2E%22">Anderson, Edward A.</searchLink> (ORCID <externalLink term="http://orcid.org/0000-0002-4149-0494">0000-0002-4149-0494</externalLink>)<br /><searchLink fieldCode="AR" term="%22Burton%2C+Jonathan+W%2E%22">Burton, Jonathan W.</searchLink>
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  Data: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
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  Data: Organic synthesis in a modern research laboratory uses state-of-the-art equipment to provide inert atmospheres, track reaction progress, and facilitate the purification of intermediates. Such facilities are not available in a high school laboratory. In this paper, synthetic organic chemistry is taken back to basics: A four step total synthesis of a potential histamine H[subscript 3] receptor antagonist is completed by A-level students in a school laboratory using only basic equipment. In addition to its bioactivity, the target molecule was selected on the basis of its potentially crystalline nature, allowing for the purification of intermediates by recrystallization. A synthetic route was developed that could be conducted without the need for inert conditions and with intermediates stable enough to be left from one week to the next, with characterization of intermediates and the target compound carried out by collaboration with researchers and analytical facilities at the University of Oxford (U.K.). By working on the project, students not only developed their practical chemistry and problem solving skills, but also experienced the thrill of discovery that inspires people to be scientists.
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