反应详情

温度

0 °C

To a solution of the product from Example 4 (1.2 g, 4.78 mmol) and TEA (0.97 g, 9.56 mmol) in dichloromethane (100 ml) at 0° C. was added trifluoroacetic anhydride (1.2 g, 5.74 mmol). The reaction mixture was stirred at 0° C. for 1 h and evaporated to a residue, which was filtered through silica (ethyl acetate/hexane: 2/8). The fractions containing the protected amine were combined and concentrated to a residue that was dissolved in acetic acid (5 mL) and cooled to 0° C. Bromine (0.91 g, 5.74 mmol) was added and the reaction mixture stirred at this temperature for 30 min. The solid that formed was collected by filtration and dissolved in a mixture of methanol in water (1:1, 20 mL). To this solution was added 1 N aqueous sodium hydroxide (3 mL) and the mixture was stirred at room temperature overnight. Volatiles were evaporated and the desired compound was extracted with dichloromethane and transformed to hydrochloride salt, which was recrystallized from methanol-diethyl ether. Analysis. Calcd. for C14H16BrNO.HCl.0.2 CH3OH: C, 65.39; H, 7.21; N, 5.56. Found: C, 65.16; H, 7.07; N, 5.42.

1. customevaporated to a residue, which
2. filtrationwas filtered through silica (ethyl acetate/hexane: 2/8)
3. additionThe fractions containing the protected amine
4. concentrationconcentrated to a residue that
5. dissolutionwas dissolved in acetic acid (5 mL)
6. temperaturecooled to 0° C
7. stirringthe reaction mixture stirred at this temperature for 30 min
8. customThe solid that formed
9. filtrationwas collected by filtration
10. dissolutiondissolved in a mixture of methanol in water (1:1, 20 mL)
11. additionTo this solution was added 1 N aqueous sodium hydroxide (3 mL)
12. stirringthe mixture was stirred at room temperature overnight
13. customVolatiles were evaporated
14. extractionthe desired compound was extracted with dichloromethane
15. customwas recrystallized from methanol-diethyl ether