Reacción #156544

Ecuación de reacción

5-amino-6-nitroisoindoline-1,3-dione

(R)-3-aminopropane-1,2-diol

imidazole

→

solid

Rendimiento 83.2%

(R)-5-Amino-2-(2,3-dihydroxypropyl)-6-nitroisoindoline-1,3-dione

Rendimiento 83.2%

Disolventes

pentanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturato reflux
3. 3
   Temperaturamaintained for 8 h
4. 4
   FiltraciónThe precipitate was filtered
5. 5
   Lavadowashed with heptanes
6. 6
   Otrodried

Procedimiento

A mixture of 5-amino-6-nitroisoindoline-1,3-dione (2.27 g, 10.98 mmol), (R)-3-aminopropane-1,2-diol (1.0 g, 10.98 mmol), and imidazole (0.75 g, 10.98 mmol) in 100 mL of pentanol was heated to reflux and maintained for 8 h and allowed to cool down to rt. The precipitate was filtered and washed with heptanes and dried to give a yellow crystalline solid (2.57 g, 9.14 mmol, 83%). 1H NMR (500 MHz, DMSO-d6) δ 8.38 (s, 2H), 8.31 (s, 1H), 7.45 (1, 1H), 4.90 (d, J=5.0 Hz, 1H), 4.66 (t, J=5.5 Hz, 1H), 3.82-3.74 (m, 1H), 3.55 (d, J=6.5 Hz, 2H), 3.42-3.18 (m, 2H). ESI MS: m/z 279.8 (M−1).

Fuente