반응 #90428

반응 방정식

NH4Cl

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

Epibromohydrin

epibromohydrin

→

desired product

수율 49.2%

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

수율 49.2%

반응 조건

후처리

1. 1
   기타in anhydrous degassed THF
2. 2
   workup.ADDITIONA solution of n-BuLi (0.082 mL, 1.78 M in hexanes) was added dropwise
3. 3
   온도to 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
   기타to quench
7. 7
   기타the reaction
8. 8
   추출the mixture was extracted with EtOAc (3×)
9. 9
   세척The combined organic layers were washed with brine
10. 10
    건조dried over Na2SO4
11. 11
    여과filtered
12. 12
    농축concentrated
13. 13
    기타The crude residue was purified by chromatography (SiO2, 0-50% EtOAc/Hexane)

실험 절차

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%).

출처