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Benzyl Bromide → methyl 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionate

HRID 259830
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 259830
Cl.[NH2:2][C@@H:3]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH2:21]([N:2]([C@@H:3]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[C:4]([O:6][CH3:7])=[O:5])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22861687methyl (2S)-2-amino-3-cyclohexylpropanoate hydrochloride

Produkt 1

HCID 22861690methyl 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionateAusbeute 165,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Methyl 2(S)-amino-3-cyclohexylpropionate hydrochloride (150 g) was dissolved in N,N-dimethylformamide (1200 ml). Thereto was added pulverized potassium carbonate (330.7 g), and benzyl bromide (254.6 g) was dropwise added to the obtained suspension while stirring. After the dropwise addition, the inner temperature was raised to 50° C., and the reaction mixture was stirred at said temperature for 9 hours. The reaction mixture was cooled and filtered. Water (600 ml) and diisopropyl ether (600 ml) were added to the filtrate for partition, and the organic layer was separated. The water layer was re-extracted with diisopropyl ether (300 ml), and the combined organic layer was washed with 5% hydrochloric acid (600 ml), 5% aqueous sodium hydrogencarbonate (600 ml), and 25% aqueous sodium chloride sequentially and dried over magnesium sulfate. The solvent was distilled away to give 204.6 g of methyl 2(S)-(N,N-dibenzylamino)-3-cyclohexylpropionate.

Aufarbeitung

  1. additionThereto was added
  2. additionwas dropwise added to the obtained suspension
  3. additionAfter the dropwise addition
  4. stirringthe reaction mixture was stirred
  5. customfor 9 hours
  6. temperatureThe reaction mixture was cooled
  7. filtrationfiltered
  8. additionWater (600 ml) and diisopropyl ether (600 ml) were added to the filtrate
  9. customfor partition
  10. customthe organic layer was separated
  11. extractionThe water layer was re-extracted with diisopropyl ether (300 ml)
  12. washthe combined organic layer was washed with 5% hydrochloric acid (600 ml), 5% aqueous sodium hydrogencarbonate (600 ml), and 25% aqueous sodium chloride sequentially
  13. dry with materialdried over magnesium sulfate
  14. distillationThe solvent was distilled away

Quellen und Nachweise

ORD-Eintrag
ord-85783abc216c48f4ba83c5bfc44774a9
Quelldatensatz
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05523410

Notizen zur Reaktion

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