Morpholine → HCID 9823153, compound

HRID 1790999Notes

Reaction equation

HRID 1790999 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6]/[CH:7]=[C:8]1\[CH2:9][C@@H:10]2[C@H:14]([CH2:15]\1)[C@@H:13](/[CH:16]=[CH:17]/[C@@H:18]([OH:25])[CH:19]([CH3:24])[CH2:20][C:21]#[C:22][CH3:23])[C@H:12]([OH:26])[CH2:11]2)(O)=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.[Cl-].[NH4+]>CN(C)C=O>[O:42]1[CH2:43][CH2:44][N:39]([CH2:1][CH2:4][CH2:5][CH2:6]/[CH:7]=[C:8]2\[CH2:9][C@@H:10]3[C@H:14]([CH2:15]\2)[C@@H:13](/[CH:16]=[CH:17]/[C@@H:18]([OH:25])[CH:19]([CH3:24])[CH2:20][C:21]#[C:22][CH3:23])[C@H:12]([OH:26])[CH2:11]3)[CH2:40][CH2:41]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 25517Ammonium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 5311181Iloprost

Product 1

HCID 9823153HCID 9823153, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

20 mg of (1S,2R,3R,5S)-7-[(E)-4-carboxybutylidene]-2-[(3S,1E)-3-hydroxy-4-methyl-6-octyne-1-enyl]-3-hydroxybicyclo[3.3.0]octane was taken and dissolved in 2 mL of dimethylformamide. After addition of 20 mg of 1,1′-carbonyldiimidazole, it was stirred at 50° C. for 1.5 hours. It was then cooled to ambient temperature, and 100 mg of morpholine was added. After stirring at 50° C. for 2 hours, an aqueous solution saturated with ammonium chloride was added and extraction was performed with ethyl acetate. The organic layer was washed with a saturated saline solution, and dried with anhydrous sodium sulfate. After filtration and concentration, 3 mL of tetrahydrofurane was added. While stirring, 100 mg of lithium aluminium hydride was added, and stirring continued at 50° C. for 3 hours. While stirring at ambient temperature, 200 μL of an aqueous solution saturated with sodium sulfate was added, then 1 g of anhydrous sodium sulfate was added, and stirred for 16 hours. A filtration was performed over celite, and after washing the residue with ethyl acetate, the filtrate was concentrated and subjected to a silicagel column chromatography, to obtain 7 mg of the compound presented in the title (40% yield).

Workup

  1. temperatureIt was then cooled to ambient temperature
  2. stirringAfter stirring at 50° C. for 2 hours
  3. extractionextraction
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationAfter filtration and concentration, 3 mL of tetrahydrofurane
  7. additionwas added
  8. stirringWhile stirring
  9. addition100 mg of lithium aluminium hydride was added
  10. stirringstirring
  11. waitcontinued at 50° C. for 3 hours
  12. stirringWhile stirring at ambient temperature
  13. addition200 μL of an aqueous solution saturated with sodium sulfate was added
  14. addition1 g of anhydrous sodium sulfate was added
  15. stirringstirred for 16 hours
  16. filtrationA filtration
  17. washafter washing the residue with ethyl acetate
  18. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4a78a9a85ece421eb143a32bead65125
Source dataset
uspto-grants-2006_07
Patent number
US07071359B1

Reaction notes

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