Using Organo-Catalysis to Synthesize One Side of Lipitor

Material Information

Title:
Using Organo-Catalysis to Synthesize One Side of Lipitor
Series Title:
Student Symposium 2016
Creator:
Murphy, Alexandra ( Author, Primary )
Ghosh, Phalguni ( Advisor )
Lavey, Brian ( Advisor )
Middlesex College, Department of Natural Sciences ( Sponsor )
Place of Publication:
Edison, NJ
Publisher:
Middlesex College
Publication Date:

Subjects

Subjects / Keywords:
College students -- poster presentations ( lcsh )
Student Works -- Natural Sciences -- poster presentations ( lcsh )
Chemistry ( lcsh )
Biochemistry ( lcsh )
Middlesex College (Edison, NJ) -- Student works
Middlesex County College (Edison, NJ) ( lcsh )
Student works -- Natural Sciences -- Academic theses
Temporal Coverage:
Academic Year 2016-2017 ( 2016 - 2017 )
Spatial Coverage:
New Jersey -- Edison

Notes

Abstract:
For this project, a new synthesis of the key precursor for Lipitor (as well as other statin drugs) was attempted. This involved a series of reactions, some of which were to create materials which were not present in the lab, and some of which were essential to the production of the compound. First, we carried out an acylation reaction between 2-naphthoyl chloride and aminoacetaldehyde dimethyl acetal with triethylamine to act as a base and ethyl acetate as a solvent. Then, that product underwent a hydrolysis using THF and 2M HCl to convert the acetal to an aldehyde which went in about 80% yield. Next, L-proline was used to catalyze a reaction in conjunction with DMSO to add 2 equivalents of acetaldehyde to the aldehyde product, which should result in two hydroxyl groups facing forward due to syn addition. L-proline acts to add the hydroxyl groups in a stereochemically-specific way, which should be the syn conformation. That reaction was based on a publishing in the Journal of the American Chemical Society by Carlos F. Barbas III, et al. The product of this reaction can cyclize, which was seen in this case. The next reaction involved protecting the hydroxyl groups before an oxidation reaction to convert the aldehyde to a carboxylic acid. This is where research ended for this project and where future researchers can pick up at.

Record Information

Source Institution:
Middlesex County College Institution
Holding Location:
Middlesex County College Institution
Rights Management:
All applicable rights reserved by the source institution and holding location.

MCC Membership

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