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Regioselective Reduction of N-Alkyl-3-sulfonyl Glutarimides to δ-Lactams. Formal Synthesis of (.+-.)-Paroxetine and (.+-.)-Tacamonine.

✍ Scribed by Chung-Yi Chen; Bo-Rui Chang; Min-Ruei Tsai; Meng-Yang Chang; Nein-Chen Chang

Book ID
101954710
Publisher
John Wiley and Sons
Year
2004
Weight
114 KB
Volume
35
Category
Article
ISSN
0931-7597

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Regioselective reduction of N-alkyl-3-su
Regioselective reduction of N-alkyl-3-sulfonyl glutarimides. Synthesis of 3,4-dihydro-3-tosylpyridin-2-ones
✍ Bo-Rui Chang; Chung-Yi Chen; Nein-Chen Chang 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 57 KB

Treatment of N-alkyl-3-sulfonyl glutarimides (1) with sodium hydride and then lithium aluminum hydride could give regioselective reduced hydroxy piperidones (5) which were further dehydrated to 3,4-dihydro-3-tosylpyridin-2-ones (6) in the presence of boron trifluoride.