Methylamine → Ispronicline

HRID 324265

반응식

HRID 324265 반응식
[CH:1]([O:4][C:5]1[CH:6]=[C:7](/[CH:11]=[CH:12]/[CH2:13][C@H:14](O)[CH3:15])[CH:8]=[N:9][CH:10]=1)([CH3:3])[CH3:2].[CH3:17][NH2:18]>C(O)C>[CH3:17][NH:18][C@H:14]([CH2:13]/[CH:12]=[CH:11]/[C:7]1[CH:8]=[N:9][CH:10]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:6]=1)[CH3:15]

참가 물질

4

반응물 2

HCID 6329MethylamineHCID 12052266(2R)-(4E)-5-(5-isopropoxy-3-pyridyl)-4-penten-2-ol

생성물 1

HCID 9824145Ispronicline수율 31%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of (2R)-(4E)-5-(5-isopropoxy-3-pyridyl)-4-penten-2-ol ptoluenesulfonate (11.00 g, 29.33 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 2.10 g (31.0%) 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-0db98d2c0d9b4760adfdef02cbd040db
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218383B1

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