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Reactions of 4-oxoalkanoic acids. III. Synthesis of 5-Methyl- and 5-Methylenepyrrolidin-2-ones by reaction of α-angelica lactone with methylamine

✍ Scribed by Dr. Christine Wedler; Dr. sc. nat. Burkhard Costisella; Prof. Dr. sc. nat. Hans Schick

Book ID
105353720
Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
385 KB
Volume
332
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

A re‐examination of the reaction of α‐angelica lactone with methylamine in water confirmed that 5‐hydroxy‐1,5‐dimethylpyrrolidin‐2‐one (5) was formed almost quantitatively in a very fast reaction. Dehydration of this compound by vacuum distillation, however, unexpectedly afforded 1‐methyl‐5‐methylenepyrrolidin‐2‐one (6), a compound with an exocyclic double bond, but not the isomeric 1,5‐dimethyl‐4‐pyrrolin‐2‐one (7) with an endocyclic double bond, as earlier claimed in the literature. With an excess of methylamine in methanol α‐angelica lactone was transformed into 5‐methylamino‐1,5‐dimethylpyrrolidin‐2‐one (8). This re‐examination was made to get levulinic acid derivatives with potential suitability for new syntheses of 1,4‐dicarbonyl compounds.

📜 SIMILAR VOLUMES

Reactions of 4-Oxoalkanoic Acids, 4. Syn
Reactions of 4-Oxoalkanoic Acids, 4. Synthesis of (±)-6-Alkyl-5-oxa-1-azabicyclo[4.3.0]nonan-9-ones, (±)-5-Alkyl-4-oxa-1-azabicyclo[3.3.0]octan-8-ones, and Substituted 1,6-Dioxa-3,8-diazacyclodecanes by Reaction of Ethyl 4-Oxoalkanoates with 3-Aminopropanol and 2-Aminoethanol
✍ Wedler, Christine ;Schick, Hans ;Scharfenberg-Pfeiffer, Doris ;Reck, Günter 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 432 KB

## Abstract Ethyl 4‐oxoalkanoates 1 react at ambient temperature in dry methanol in the presence of molecular sieve 3 Å in almost quantitative yield with 3‐aminopropanol and 2‐aminoethanol to form the bicyclic lactams __rac__‐2 and __rac__‐3, respectively. Surprisingly, the (±)‐5‐alkyl‐4‐oxa‐1‐azab