1-Aminocyclohexanecarboxylic acid → 2-Cyclopentyl-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

HRID 73841

Reaktionsgleichung

Reaktionsgleichung von HRID 73841
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1([C:16](O)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Na+].[Na+].Cl.C(N=C=NCCCN(C)C)C>C(OCC)(=O)C.O>[CH:1]1([C:6]2[O:7][C:16](=[O:17])[C:10]3([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 13661-Aminocyclohexanecarboxylic acidHCID 10340Sodium CarbonateHCID 78284Cyclopentanecarbonyl chlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 247401222-Cyclopentyl-3-oxa-1-azaspiro[4.5]dec-1-en-4-oneAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

1.98 g (15 mmol) of cyclopentanecarbonyl chloride was added to a solution of 2.16 g (15 mmol) of 1-aminocyclohexanecarboxylic acid and 4.8 g (45 mmol) of sodium carbonate in 50 ml of ethyl acetate-50 ml of water under ice-cooling. After the mixture was stirred at room temperature overnight, ethyl acetate was added thereto, and the mixture was washed with a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium bicarbonate solution and then saturated brine. After the obtained organic layer was washed with saturated brine, it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, methylene chloride was added thereto, and under ice-cooling, 1.59 g (8.3 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added. After the mixture was stirred at room temperature overnight, under reduced pressure, the reaction solution was concentrated, ethyl acetate was added thereto, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 1.41 g (42%) of the title compound.

Aufarbeitung

  1. temperaturecooling
  2. washthe mixture was washed with a 10% aqueous potassium hydrogensulfate solution
  3. washAfter the obtained organic layer was washed with saturated brine, it
  4. dry with materialwas dried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure, methylene chloride
  6. additionwas added
  7. temperatureunder ice-cooling
  8. stirringAfter the mixture was stirred at room temperature overnight, under reduced pressure
  9. concentrationthe reaction solution was concentrated
  10. additionethyl acetate was added
  11. washthe mixture was successively washed with water
  12. dry with materialby drying with anhydrous sodium sulfate
  13. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bce3cbce48a14e97a14fd7c56094ad70
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829209B2

Verknüpfte Notizen

Wird geladen…