反应详情

Tyramine (5.27 g), glacial acetic acid (5.27 g), estrone methyl ether (4.92 g) sodium cyanoborohydride (1.09 g), tetrahydrofuran (43 ml) were added to methanol (58 ml). The reacting mixture was allowed to stir for 21 hours at room temperature. TLC (ethyl acetate) revealed the formation of a more polar product (Rf 0.25). After 19 hours TLC revealed that the starting material still remained in the reaction solution. The system was warmed at 40° C. in an oil bath. The solution remained as a white undissolved solid. After 29 hours the system was allowed to reach room temperature. Excess solvent was removed under reduced pressure. Water was added and made basic (pH 9) with aqueous 50% NAOH. The white solid did not dissolve in ether and was slightly soluble in ethyl acetate. The solid was filtered and mixed with 34 g of flash silica gel and ethyl acetate. The solvent was removed under reduced pressure. The silica gel was poured on top of the chromatographic column, The compound was eluted with ethyl acetate. Solid was obtained and was recrystallized from ethyl acetate, mp 184°-185° C. (diabetes)

1. waitAfter 19 hours TLC revealed that the starting material
2. temperatureThe system was warmed at 40° C. in an oil bath
3. waitAfter 29 hours the system was allowed
4. customto reach room temperature
5. customExcess solvent was removed under reduced pressure
6. additionWater was added
7. dissolutionThe white solid did not dissolve in ether
8. filtrationThe solid was filtered
9. additionmixed with 34 g of flash silica gel and ethyl acetate
10. customThe solvent was removed under reduced pressure
11. additionThe silica gel was poured on top of the chromatographic column
12. washThe compound was eluted with ethyl acetate
13. customSolid was obtained
14. customwas recrystallized from ethyl acetate, mp 184°-185° C. (diabetes)