تفاعل #595397

معادلة التفاعل

NH4Cl

Ethyl 8-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Epibromohydrin

epibromohydrin

→

desired product

المردود 49.2%

Ethyl 8-Methyl-5-(oxiran-2-ylmethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

المردود 49.2%

ظروف التفاعل

المعالجة

1. 1
   أخرىin anhydrous degassed THF
2. 2
   workup.ADDITIONA solution of n-BuLi (0.082 mL, 1.78 M in hexanes) was added dropwise
3. 3
   درجة الحرارةto warm slowly to ambient temperature
4. 4
   workup.WAITAfter 3.5 h
5. 5
   workup.STIRRINGthe reaction was stirred overnight at ambient temperature
6. 6
   أخرىto quench
7. 7
   أخرىthe reaction
8. 8
   استخلاصthe mixture was extracted with EtOAc (3×)
9. 9
   غسيلThe combined organic layers were washed with brine
10. 10
    تجفيفdried over Na2SO4
11. 11
    ترشيحfiltered
12. 12
    تركيزconcentrated
13. 13
    أخرىThe crude residue was purified by chromatography (SiO2, 0-50% EtOAc/Hexane)

الإجراء التجريبي

Ethyl 8-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (0.025 g, 0.097 mmol) was dissolved in anhydrous degassed THF and was cooled to −78° C. A solution of n-BuLi (0.082 mL, 1.78 M in hexanes) was added dropwise and the reaction was stirred at −78° C. for 30 min. Epibromohydrin (0.016 mL, 0.194 mmol) was added and the reaction was allowed to warm slowly to ambient temperature. After 3.5 h, epibromohydrin (0.008 mL, 0.097 mmol) was added and the reaction was stirred overnight at ambient temperature. Upon completion, saturated aqueous NH4Cl was added to quench the reaction and the mixture was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by chromatography (SiO2, 0-50% EtOAc/Hexane) to afford the desired product (15 mg, 49%).

المصدر