Reacción #355791

Ecuación de reacción

3-(Trifluoromethyl)phenyl isocyanate

2a

2-(S)-Amino-N-(1-benzyl-pyrrolidin-3-(R)-yl)-3,3-dimethyl-butyramide

→

3a

Rendimiento 34.0%

N-(1-Benzyl-pyrrolidin-3-(R)-yl)-3,3-dimethyl-2-(S)-[3-(3-trifluoromethyl-phenyl)-ureido]-butyramide

Rendimiento 34.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was then quenched with water (20 mL)
2. 2
   Secadothe organic layer was dried over anhydrous sodium sulfate
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe organic residue was purified by flash chromatographey on silica gel
6. 6
   Lavadoeluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4)

Procedimiento

3-(Trifluoromethyl)phenyl isocyanate (0.093 g, 0.50 mmole) was slowly added to a solution of 2a (0.12 g, 0.42 mmole) in dichloromethane (20 mL) at 0° C. The solution was allowed to warm to room temperature and stirred for 18 h. The reaction was then quenched with water (20 mL), and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The organic residue was purified by flash chromatographey on silica gel, eluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4) to give 3a (0.045 g, 34%) as a white solid; MS (EI)=476 (M+).

Fuente