Reacción #607476

Ecuación de reacción

2

Ethyl 4,5,6,7-Tetrahydro-1H-indole-2-carboxylate

NaH

bromoacetonitrile

→

ethyl 1-(cyanomethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Rendimiento 55.0%

Ethyl 1-(Cyanomethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Rendimiento 55.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA 125-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
2. 2
   Otrowas purged with nitrogen
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature for 14 h
4. 4
   ConcentraciónAfter that time, the reaction mixture was concentrated under reduced pressure
5. 5
   Otrothe residue was partitioned between ethyl acetate (150 mL) and water (450 mL)
6. 6
   OtroThe organic layer was separated
7. 7
   Extracciónthe aqueous layer was extracted with ethyl acetate (3×150 mL)
8. 8
   LavadoThe combined organic layers were washed with brine
9. 9
   Secadodried over sodium sulfate
10. 10
    Concentraciónconcentrated under reduced pressure
11. 11
    OtroThe residue was purified by column chromatography

Procedimiento

A 125-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was purged with nitrogen and charged with 2 (5.76 g, 29.8 mmol) and DMF (50 mL). The solution was cooled to 0° C. using an ice bath. NaH (60% dispersion in mineral oil, 1.43 g, 35.8 mmol) was added. The resulting mixture was stirred at room temperature for 1 h. After that time, bromoacetonitrile (1.43 g, 35.8 mmol) was added. The mixture was stirred at room temperature for 14 h. After that time, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (150 mL) and water (450 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3×150 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 55% yield (3.80 g) of ethyl 1-(cyanomethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate 3 as a yellow semi-solid: 1H NMR (300 MHz, CDCl3) δ 6.66 (s, 1H), 5.29 (s, 2H), 4.28 (q, 2H, J=7.2 Hz), 2.62 (t, 2H, J=6.3 Hz), 2.49 (t, 2H, J=6.3 Hz), 1.92 (m, 2H), 1.75 (m, 2H), 1.33 (t, 3H, J=7.2 Hz); MS (ESI+) m/z 233.1 (M+H)

Fuente