تفاعل #607476

معادلة التفاعل

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

المردود 55.0%

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

المردود 55.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)

المصدر