By Jie Jack Li, Douglas S. Johnson, Drago R. Sliskovic, Bruce D. Roth
Written by way of contributors of Pfizer international examine and improvement for chemists coming into the pharmaceutical undefined, this paintings profiles the synthesis of fourteen consultant pharmaceutical items on the way to reveal the multidisciplinary nature of the pastime. for every drug, they supply a historic advent and the organic, pharmacological, pharmakinetic, and drug metabolism heritage ahead of detailing the drug's synthesis.
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Extra resources for Contemporary Drug Synthesis
Cbz protection of commercially available ethyl pipendine-4- carboxylate (34) was achieved using N-(benzyloxycarbony1oxy)succinimide to afford 35. Treatment of 35 with three equivalents phenyl magnesium bromide led to tertiary alcohol Chapter 5. Nan-sedating Antihistamines 41 36, which was then unmasked to give diphenylpiperidin-4-ylmethanol (24) via hydrogenolysis. Alkylation of 24 with alkyl chloride 37 was facilitated by KI via the Finkelstein reaction to produce dioxolane 38 which was unmasked to aldehyde 39 via acidic hydrolysis.
The SNZ displacement of the chlonde on 23 by a,a- diphenethyl-4-piperidinemethanol (24, vide infra) was aided by addition of a catalytic amount of KI via the Finkelstein reaction mechanism to give 25. Removal of the acetate protection was easily achieved using basic hydrolysis to afford neopentyl alcohol 26. Oxidation of 26 using the Swern oxidation followed by oxidation with KMn04 gave the corresponding carboxylic acid 27. The transformation 26 + 27 was also accomplished using either H5IO&CuC13-5H20 in CHC13/CH&N or K&O$RuC13*5HzO.
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