Toluene → HCID 15096977, compound

HRID 846747Notes

Reaction equation

HRID 846747 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C@H:3]1[OH:13].[C:14]1(=O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[O:15]1.CC1C=CC=CC=1>O>[O:15]=[C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:23])[N:1]1[C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C@H:3]1[OH:13]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6811Phthalic AnhydrideHCID 13677749HCID 13677749, compound

Product 1

HCID 15096977HCID 15096977, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.7 parts of ethyl trans-4-amino-3-hydroxy-1-piperidinecarboxylate, 3.7 parts of 1,3-dihydroisobenzofuran-1,3-dione and 45 parts of methylbenzene was stirred and refluxed for 2 hours using a water-separator. The reaction mixture was decanted from some insoluble tar. The methylbenzene-phase was evaporated in vacuo in a boiling water-bath. The residue was boiled in 2,2'-oxybispropane. After cooling, the solvent was decanted. The remaining oil solidified on scratching in 2,2'-oxybis-propane. The product was filtered off and dissolved in dichloromethane. The solution was washed successively with a dilute hydrochloric acid solution, water, a dilute sodium hydroxide solution and again water. The organic phase was dried, filtered and evaporated in vacuo. The residue solidified on scratching in 2,2'-oxybispropane. The product was filtered off and crystallized from 2-propanol, yielding 2.12 parts of ethyl trans-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-hydroxyl-1-piperidinecarboxylate; mp. 128.4° C. (intermediate 57).

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe reaction mixture was decanted from some insoluble tar
  3. customThe methylbenzene-phase was evaporated in vacuo in a boiling water-bath
  4. temperatureAfter cooling
  5. customthe solvent was decanted
  6. filtrationThe product was filtered off
  7. dissolutiondissolved in dichloromethane
  8. washThe solution was washed successively with a dilute hydrochloric acid solution, water
  9. customThe organic phase was dried
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. filtrationThe product was filtered off
  13. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-b4d046fea2ef46c88971fce454f0a7ba
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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