TREA

Preparation of 5-(1-alkyl-carbonyloxy)alkylpyrrolidin-2-one

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Information

  • Patent Grant
  • 4943640
  • Patent Number
    4,943,640
  • Date Filed
    Friday, March 18, 1988
    36 years ago
  • Date Issued
    Tuesday, July 24, 1990
    34 years ago
Information
Abstract
The invention is a process for the preparation of a 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-one which comprises contacting a N-alkylcarbonyl-5-alkylcarbonylpyrrolidin-2-one with hydrogen in the presence of a catalytic amount of a hydrogenation catalyst under conditions such that a 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-one is prepared.
Description
Claims
  • 1. A process for the preparation of a 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-one which comprises contacting a N-alkylcarbonyl-5-alkylcarbonylpyrrolidin-2-one with hydrogen in the presence of a catalytic amount of a hydrogenation catalyst under conditions such that a 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-one is prepared.
  • 2. The process of claim 1 wherein the N-alkylcarbonyl-5-alkylcarbonylpyrrolidin-2-one corresponds to the formula ##STR7## and the 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-one corresponds to the formula ##STR8## wherein R.sup.1 separately in each occurrence is hydrogen or C.sub.1-20 alkyl and R.sup.2 is C.sub.1-20 alkyl.
  • 3. The process of claim 2 wherein R.sup.1 is hydrogen or C.sub.1-5 alkyl and R.sup.2 is C.sub.1-5 alkyl.
  • 4. The process of claim 2 wherein R.sup.1 is hydrogen and R.sup.2 is methyl.
  • 5. The process of claim 2 wherein the reaction is run in an organic solvent which is inert to the reactants and not reducible by hydrogen.
  • 6. The process of claim 5 wherein the hydrogenation catalyst is a Group VIII metal, chromium, rhenium or iron.
  • 7. The process of claim 6 wherein the hydrogenation catalyst is palladium or platinum.
  • 8. The process of claim 7 wherein the hydrogenation catalyst is palladium.
  • 9. The process of claim 8 wherein the hydrogenation catalyst is a heterogeneous catalyst.
  • 10. The process of claim 9 wherein the support is a zeolite, silica, alumina or activated carbon.
  • 11. The process of claim 10 wherein the support is alumina.
  • 12. The process of claim 10 wherein the support is loaded with between about 0.1 and 25 percent by weight of the catalyst.
  • 13. The process of claim 12 wherein the support is loaded with between about 0.5 and 10 percent by weight of a hydrogenation catalyst.
  • 14. The process of claim 12 wherein the temperature is between about 25.degree. C. and 200.degree. C.
  • 15. The process of claim 14 wherein the temperature is between about 50.degree. C. and 150.degree. C.
  • 16. The process of claim 14 wherein the pressure is between about 14.7 and 3,000 psi.
  • 17. The process of claim 16 wherein the pressure is between about 50 and 1,500 psi.
  • 18. The process of claim 16 wherein the organic solvent is an alcohol, ether, ester, aromatic hydrocarbon or carboxylic acid.
  • 19. The process of claim 18 wherein the organic solvent is a monocarboxylic acid.
CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation-in-part of application Ser. No. 542,293, filed Oct. 14, 1983, abandoned. This invention relates to the preparation of 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-ones. The 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-ones are useful as intermediates in the preparation of pharmacologically active compounds. More particularly, these compounds can be converted to 5-(1,2-ethylenically unsaturated)alkylpyrrolidin-2-ones, which can then be converted to a 4-amino-5-alkenoic acid (see Gittos et al., U.S. Pat. No. 4,235,778, incorporated herein by reference). 4-Amino-5-alkenoic acids are pharmacologically active compounds. One 4-amino-5-alkenoic acid is 4-amino-5-hexenoic acid which is an irreversible inhibitor of y-aminobutyric acid transaminase, rendering it useful in the treatment of disorders of the central nervous system function (see Metcalf et al., U.S. Pat. No. 3,960,927, incorporated herein by reference). Presently known processes for the preparation of 5-(1,2-ethylenically unsaturated)alkylpyrrolidin-2-ones require costly reagents and complicated processing schemes. What is needed is a relatively simple process for the preparation of a precursor to the 5-(1,2-ethylenically unsaturated)alkylpyrrolidin-2-one in which relatively available and inexpensive starting reagents are used, and wherein the precursor can be pyrolyzed to the desired 5-(1,2-ethylenically unsaturated)alkylpyrrolidin-2-one. The invention is a process for the preparation of a 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-one which comprises contacting a N-alkylcarbonyl-5-alkylcarbonylpyrrolidin-2-one with hydrogen in the presence of a catalytic amount of a hydrogenation catalyst under conditions such that a 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-one is prepared. Surprisingly, a process for the preparation of a compound which can be pyrolyzed to a 5-(1,2-ethylenically unsaturated)alkylpyrrolidin-2-one in which the starting reagents are relatively available and inexpensive has been discovered. In addition to their utility as precursors to pharmacologically active compounds, the products of the process of this invention are also useful as solvents for organic compounds which are soluble in N-methylpyrrolidinone and as monomers for copolymerization with other vinyl monomers.

Foreign Referenced Citations (1)
Number Date Country
2028307 Mar 1980 GBX
Non-Patent Literature Citations (2)
Entry
Chem. Abstracts, vol. 82, 97983b, p. 438 (1975).
Lepschy et al., Justus Liebigs Ann. Chem., 1753 (1974).
Continuation in Parts (1)
Number Date Country
Parent 542293 Oct 1983