Dimethylformamide → But-3-enyl-((S)-1-phenyl-ethyl)-amine

HRID 29060

Reaktionsgleichung

Reaktionsgleichung von HRID 29060
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][CH2:9][CH:10]=[CH2:11].N[C@H:13](C(O)=O)[CH2:14][C:15]1[CH:24]=[C:23]2[C:18](C=CC=C2)=[CH:17][CH:16]=1.C[N:29](C=O)C>CCOCC>[CH2:8]([NH:29][C@H:14]([C:15]1[CH:24]=[CH:23][CH:18]=[CH:17][CH:16]=1)[CH3:13])[CH2:9][CH:10]=[CH2:11]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21241Homoallyl bromideHCID 1859152-Naphthylalanine

Produkt 1

HCID 10559173But-3-enyl-((S)-1-phenyl-ethyl)-amineAusbeute 76,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of S-(−)-1-phenyl ethylamine (15.75 g, 130 mmol) in 150 mL of DMF at 0° C. is added K2CO3 (53.9 g, 390 mmol) in small portions. After stirring at 0° C. for 10 min, 4-bromobutene (13.5 g, 100 mmol) is added dropwise and followed by Nal (58.5 g, 390 mmol) in small portions. The reaction mixture, a white suspension, is heated to 95° C. and stirred overnight/16 hrs. The solution is cooled to RT and diluted with 200 mL of ether, and washed with 3×100 ml of water. The organic layer is dried over Na2SO4 and concentrated. The crude product is purified by distillation (65˜70° C. under high vacuum) to yield a colorless liquid(13.5 g, 76.7%). (NMR and MS data confirmed, U-4117-28-23).

Aufarbeitung

  1. temperatureThe reaction mixture, a white suspension, is heated to 95° C.
  2. stirringstirred overnight/16 hrs
  3. temperatureThe solution is cooled to RT
  4. washwashed with 3×100 ml of water
  5. dry with materialThe organic layer is dried over Na2SO4
  6. concentrationconcentrated
  7. distillationThe crude product is purified by distillation (65˜70° C. under high vacuum)

Quellen und Nachweise

ORD-Eintrag
ord-e18d2c92ed544433ac683fe4fc95cb76
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419975B2

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