Methylamine → Ispronicline

HRID 489762ノート

反応式

HRID 489762 の反応式
C1(C)C=CC(S(O[C@@H:11]([CH2:13]/[CH:14]=[CH:15]/[C:16]2[CH:17]=[N:18][CH:19]=[C:20]([O:22][CH:23]([CH3:25])[CH3:24])[CH:21]=2)[CH3:12])(=O)=O)=CC=1.[CH3:27][NH2:28]>C(O)C>[CH3:27][NH:28][C@H:11]([CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:17]=[N:18][CH:19]=[C:20]([O:22][CH:23]([CH3:25])[CH3:24])[CH:21]=1)[CH3:12]

参加物

4

反応物 2

HCID 6329MethylamineHCID 12052269(2R)-(4E)-5-(5-isopropoxy-3-pyridyl)4-penten-2-ol p-toluenesulfonate

生成物 1

HCID 9824145Ispronicline収率 31%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of (2R)-(4E)-5-(5-isopropoxy-3-pyridyl)-4-penten-2-ol p-toluenesulfonate (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.

後処理

  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

出典と根拠

ORDレコード
ord-47bb5819c250498f956438520bc3bed6
出典データセット
uspto-grants-2005_12
特許番号
US06979695B2

反応ノート

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