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Synthesis of ethyl 1-azabicyclo[2.2.1]hept-4-yl carboxylate

✍ Scribed by Barry S. Orlek; Harry Wadsworth; Paul Wyman; Frank D. King

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
117 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis

The dipolar cycloaddition reaction of a-methylene butyrolactone and N-benzyl azomethine ylid (5) affords the spirolactone (2) which rearranges to give ethyl 1-azabicyclo[2.2.l]hept-Cyl carboxylate (1) in excellent overall yield.

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Synthesis of some 4-acyloxy-7-oxo-1-azab
Synthesis of some 4-acyloxy-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylates
✍ John H. Bateson; Alison M. Quinn; Robert Southgate 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 188 KB

Allylic oxidation of 4-allyl-1-dimethyl-t-butylsilylazetidin-2ones (5,7) gave the 4-(l-hydroxyprop-2-ene-1-yl) derivatives (6,8). Radical benzoyloxylation of the silylated 8-oxo-7-azabicyclo[4.2.O]oct-3ene (18) provided four allylic monobenzoates. Progression of ( ) and ( ) afforded, respectively,