Реакция #710557

Уравнение реакции

HCl

(Z)-tert-butyl 2-((4-(dimethylcarbarnoyl)-phenoxy)methyl)-3-fluoroallylcarbamate

trifluoroacetic acid

→

(Z)-4-(2-(aminomethyl)-3-fluoroallyloxy)-N,N-dimethylbenzamide hydrochloride

Выход 71.0%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   ДругоеAll volatiles were removed in vacuo
2. 2
   Другоеto remove trifluoroacetic acid
3. 3
   ДругоеThe precipitate formed
4. 4
   Другоеwas isolated
5. 5
   Другоеdried under reduced pressure

Методика

To a stirring solution of (Z)-tert-butyl 2-((4-(dimethylcarbarnoyl)-phenoxy)methyl)-3-fluoroallylcarbamate (520.0 mg, 1.48 mmol) in CH2Cl2 (8.0 mL) at room temperature was added trifluoroacetic acid (2.0 mL). The resulting mixture was stirred at room temperature for 30 min. All volatiles were removed in vacuo and the residue was co-evaporated with CH2Cl2 (2×20 mL) to remove trifluoroacetic acid. The resulting oil was taken up in ethyl acetate (3.0 mL) and then ethereal HCl (2.0 M in diethyl ether; 1.0 mL, 2.0 mmol) was added. The precipitate formed was isolated and dried under reduced pressure to afford (Z)-4-(2-(aminomethyl)-3-fluoroallyloxy)-N,N-dimethylbenzamide hydrochloride (301 mg, 71%) as a pale yellow solid; m.p.=135-137° C.; 1H-NMR (300 MHz; MeOD) δ ppm: 3.06 (3H, br s), 3.10 (3H, br s), 3.71 (2H, d, J 3.0 Hz), 4.88 (2H, dd, J 2.8, 0.8 Hz), 7.11 (2H, d, J 8.9 Hz), 7.13 (1H, d, J 80.8 Hz), 7.45 (2H, d, J 8.9 Hz).

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