Methylamine → 4-Penten-2-amine, N-methyl-5-(3-pyridinyl)-, (2S,4E)-

HRID 1824746노트

반응식

HRID 1824746 반응식
C1(C)C=CC(S(O[C@@H:11]([CH2:13]/[CH:14]=[CH:15]/[C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH3:12])(=O)=O)=CC=1.[CH3:23][NH2:24]>C(O)C>[CH3:23][NH:24][C@H:11]([CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH3:12]

참가 물질

4

반응물 2

HCID 6329MethylamineHCID 87466997(2R)-(4E)-5-(3-Pyridyl)4-penten-2-ol p-Toluenesulfonate

생성물 1

HCID 98341074-Penten-2-amine, N-methyl-5-(3-pyridinyl)-, (2S,4E)-수율 24%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of (2R)-(4E)-5-(3-pyridyl)-4-penten-2-ol p-toluenesulfonate (9.00 g, 28.35 mmol), methylamine (200 mL, 40% solution in water), and ethyl alcohol (10 mL) was stirred at ambient temperature for 18 h. The resulting solution was extracted with chloroform (3×100 mL). The combined chloroform extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography over aluminum oxide, eluting with ethyl acetate-methanol (7:3, v/v). Selected fractions were combined and concentrated by rotary evaporation, producing an oil. Further purification by vacuum distillation furnished 1.20 g (24.0%) of a colorless oil, bp 90–100° C. at 0.5 mm Hg.

후처리

  1. extractionThe resulting solution was extracted with chloroform (3×100 mL)
  2. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customThe crude product was purified by column chromatography over aluminum oxide
  6. washeluting with ethyl acetate-methanol (7:3
  7. concentrationconcentrated by rotary evaporation
  8. customproducing an oil
  9. customFurther purification
  10. distillationby vacuum distillation

출처 및 근거

ORD 기록
ord-d7323c1220e44be781a633770600f65b
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045538B2

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