Реакция #710551

Уравнение реакции

Triethylamine

D-(+)-Ribonic acid gamma-lactone

methanol

3-Hydroxytyramine

→

dopamine ribonamide

Выход 188.1%

Растворители

acetone

Условия реакции

Обработка

1. 1
   workup.DISSOLUTIONuntil dissolved
2. 2
   Другоеan additional 5 min
3. 3
   workup.DISSOLUTIONto dissolve
4. 4
   workup.STIRRINGwith stirring, over the course of about 10 minutes
5. 5
   Температураthe reaction mixture refluxed for 4 hr
6. 6
   ДругоеSolvents were removed by rotary evaporation
7. 7
   Другоеto remove any residual water
8. 8
   Другое(1 hr.)
9. 9
   Другоеto give a white solid
10. 10
    Другоеagain resulting in a white solid as a product
11. 11
    ФильтрацияThe resultant solid was collected by filtration
12. 12
    Другоеdried in vacuo for 6 hrs

Методика

D-(+)-Ribonic acid gamma-lactone (2.0 gm, 13.5 mmol) was added to methanol (25 mL) in a 100 mL round bottom flask with stirring until dissolved, and then an additional 5 min. 3-Hydroxytyramine (2.6 gm, 13.5 mmol) was added slowly, allowing it to dissolve, with stirring, over the course of about 10 minutes. Triethylamine (1.4 gm, 13.5 mmol) was then added and the reaction mixture refluxed for 4 hr. in the dark, during which time the solution acquired a slight yellow color. Solvents were removed by rotary evaporation using anhydrous ethanol as an azeotrope to remove any residual water. The resultant dried product constituted a thick syrup which solidified upon standing (1 hr.) to give a white solid. The white solid product was stirred (1 hr.) with acetone (40 mL), again resulting in a white solid as a product. The resultant solid was collected by filtration and dried in vacuo for 6 hrs. yielding dopamine ribonamide (3.83 gm, 12.7 mmol, 94.1% yield.) 1H and 13C-NMR results and CHN analyses were consistent with structure. Molting point was 90-91° C. Predicted C13H19N1: (301.30): C, 51.82; H, 6.36; N, 4.65; Analysis results of synthesis product: C, 51.67; H, 6.40; N, 4.69.

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