Hydrochloric Acid → tert-Butyl (4-oxo-4-phenylbutyl)carbamate

HRID 270486

Reaktionsgleichung

Reaktionsgleichung von HRID 270486
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]1([Mg]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:12][CH2:11][CH2:10][C:9](=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3790001-Pyrrolidinecarboxylic acid, 2-oxo-, 1,1-dimethylethyl esterHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 14267858tert-Butyl (4-oxo-4-phenylbutyl)carbamateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (7.03 g, 38 mmol) in THF (130 mL) was added phenylmagnesium bromide (1.0 M solution, 50 mL) at −78° C. After stirring for 2 hour at −78° C., HCl (2 M, 35 mL) was added to quench the reaction, which was then warmed to room temperature and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organics were washed with brine (50 mL) and dried over Na2SO4, filtered and concentrated under reduced pressure to afford 9.56 g (96% yield) of the desired product.

Aufarbeitung

  1. customto quench
  2. customthe reaction, which
  3. temperaturewas then warmed to room temperature
  4. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  5. washThe combined organics were washed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7d256010abd643459ec6b150aeb763fd
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449486B2

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