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

HRID 1711510노트

반응식

HRID 1711510 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-2ead212524bf4c3d94616b15c6861429
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790757B2

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