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

HRID 332087

反応式

HRID 332087 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[CH2:20]([CH:22]1[O:24][CH2:23]1)Br.[NH4+].[Cl-]>>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:20][CH:22]3[CH2:23][O:24]3)[C:6]3[CH2:11][CH2:12][N:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

参加物

4

反応物 3

HCID 18430Epibromohydrin2 回HCID 25517Ammonium ChlorideHCID 2937007ethyl 8-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

生成物 1

HCID 58097199ethyl 8-Methyl-5-(oxiran-2-ylmethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate収率 49.2%

反応条件

温度
-78 °C

実験手順

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%).

後処理

  1. customin anhydrous degassed THF
  2. additionA solution of n-BuLi (0.082 mL, 1.78 M in hexanes) was added dropwise
  3. temperatureto warm slowly to ambient temperature
  4. waitAfter 3.5 h
  5. stirringthe reaction was stirred overnight at ambient temperature
  6. customto quench
  7. customthe reaction
  8. extractionthe mixture was extracted with EtOAc (3×)
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude residue was purified by chromatography (SiO2, 0-50% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-7ff12641939f46c3b336acf438448f35
出典データセット
uspto-grants-2014_11
特許番号
US08877797B2

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