Methylamine → Ispronicline

HRID 324265

Reaction equation

HRID 324265 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 9824145IsproniclineYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0db98d2c0d9b4760adfdef02cbd040db
Source dataset
uspto-grants-2001_04
Patent number
US06218383B1

Linked notes

Loading…