TREA

Hydride reduction process for preparing quinolone intermediates

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Information

  • Patent Application
  • 20070232806
  • Publication Number
    20070232806
  • Date Filed
    March 26, 2007
    18 years ago
  • Date Published
    October 04, 2007
    18 years ago
Information
Abstract
Hydride process for making acyclic diol intermediates from cyclic intermediates, useful in antibacterial quinolone synthesis.
Description
Claims
  • 1. A process for preparing a quinolone intermediate having the formula:
  • 2. A process according to claim 1, wherein the alkanol is a C1 to C4 alkanol.
  • 3. A process according to claim 1, wherein the ether is a C2 to C6 ether.
  • 4. A process according to claim 2, wherein the ether is a C2 to C6 ether.
  • 5. A process according to claim 1, wherein X is C1-C4 alkyl.
  • 6. A process according to claim 5, wherein X is methyl.
  • 7. A process according to claim 1, wherein Z is tert-butoxycarbonyl.
  • 8. A process according to claim 5, wherein Y is methyl.
  • 9. A process according to claim 1, wherein the calcium salt is selected from the group consisting of calcium chloride and calcium bromide.
  • 10. A process according to claim 9, wherein the calcium salt is calcium chloride.
  • 11. A process according to claim 1, wherein the compound of Formula (II) is (2S,4S)-1-(1,1-dimethylethyl)-4-methyl-5-oxo-1,2-pyrrolidinedicarboxylic acid-2-methyl ester.
  • 12. A process according to claim 1, wherein the compound of Formula (II) is (2S,4R)-1-(1,1-dimethylethyl)-4-methyl-5-oxo-1,2-pyrrolidinedicarboxylic acid-2-methyl ester.
  • 13. A process according to claim 1, wherein the compound of Formula (I) is (1S,3S)-(4-Hydroxyl-1-hydroxymethyl-3-methyl-butyl)-carbamic acid tert-butyl ester:
  • 14. A process according to claim 1, wherein the compound of Formula (I) is (1S,3R)-(4-Hydroxyl-1-hydroxymethyl-3-methyl-butyl)-carbamic acid tert-butyl ester:
  • 15. A process according to claim 1, wherein the alkanol solvent is selected from the group consisting of methanol, ethanol, propanol, isopropanol, and butanol.
  • 16. A process according to claim 15, wherein the alkanol solvent is ethanol.
  • 17. A process according to claim 1, wherein the ether solvent is selected from the group consisting of methyl tert-butyl ether (MTBE), ethylene glycol dimethyl ether, diethyl ether, tetrahydrofuran, diisopropyl ether, and dioxane.
  • 18. A process according to claim 17, wherein the ether solvent is methyl tert-butyl ether.
  • 19. A process according to claim 16, wherein the ether solvent is methyl tert-butyl ether.
  • 20. A process according to claim 19, wherein the solvent ratio (v/v) of ethanol to methyl tert-butyl ether is about 1:2.
Provisional Applications (1)
Number Date Country
60786450 Mar 2006 US