Reaction #657296

Reaction equation

Triethylamine

D-(+)-Ribonic acid gamma-lactone

methanol

3-Hydroxytyramine

→

dopamine ribonamide

Yield 188.1%

Solvents

acetone

Conditions

Workup

1. 1
   workup.DISSOLUTIONuntil dissolved
2. 2
   Otheran additional 5 min
3. 3
   workup.DISSOLUTIONto dissolve
4. 4
   workup.STIRRINGwith stirring, over the course of about 10 minutes
5. 5
   Temperaturethe reaction mixture refluxed for 4 hr
6. 6
   OtherSolvents were removed by rotary evaporation
7. 7
   Otherto remove any residual water
8. 8
   Other(1 hr.)
9. 9
   Otherto give a white solid
10. 10
    Otheragain resulting in a white solid as a product
11. 11
    FiltrationThe resultant solid was collected by filtration
12. 12
    Otherdried in vacuo for 6 hrs

Procedure

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. Melting 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.

Source