Reaction #710557

Reaction equation

HCl

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

trifluoroacetic acid

→

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

Yield 71.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherAll volatiles were removed in vacuo
2. 2
   Otherto remove trifluoroacetic acid
3. 3
   OtherThe precipitate formed
4. 4
   Otherwas isolated
5. 5
   Otherdried under reduced pressure

Procedure

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).

Source