HCID 59855131, Verbindung → (S)-Methyl 4-(dimethylamino)-3-(4-hydroxyphenyl)-4-oxobutanoate

HRID 2246667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2246667
[CH3:1][N:2]([CH3:35])[C:3](=[O:34])[C@H:4]([C:10]1[CH:15]=[CH:14][C:13]([O:16]CC2C=C(C3C=CC(C(F)(F)F)=CC=3)C=CC=2)=[CH:12][CH:11]=1)[CH2:5][C:6]([O:8][CH3:9])=[O:7]>CCOC(C)=O>[CH3:35][N:2]([CH3:1])[C:3](=[O:34])[C@H:4]([C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)[CH2:5][C:6]([O:8][CH3:9])=[O:7]

Komponenten

3

Edukt 1

HCID 59855131HCID 59855131, Verbindung

Produkt 1

HCID 59855130(S)-Methyl 4-(dimethylamino)-3-(4-hydroxyphenyl)-4-oxobutanoateAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dimethylamide 22.1 (2.1 g, 4.23 mmol) was dissolved in 50 mL of EtOAc, and nitrogen was bubbled through the solution for 5 minutes. 1 g of palladium on carbon (5 wt. %, wet contains 50% water) was added, and a hydrogen balloon was attached. After 8 hours, the mixture was filtered through a plug of silica with 10% MeOH in EtOAc. The organic layer was concentrated under reduced pressure and partitioned between ACN (100 mL) and hexane (50 mL). The ACN layer was washed with hexane (4×50 mL). The ACN layer was concentrated under reduced pressure to afford (S)-methyl 4-(dimethylamino)-3-(4-hydroxyphenyl)-4-oxobutanoate 22.2 (1.0 g, 3.98 mmol) as a colorless oil. MS ESI (pos.) m/e: 252.4 (M+H)+.

Aufarbeitung

  1. customnitrogen was bubbled through the solution for 5 minutes
  2. addition1 g of palladium on carbon (5 wt. %, wet contains 50% water) was added
  3. filtrationthe mixture was filtered through a plug of silica with 10% MeOH in EtOAc
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. custompartitioned between ACN (100 mL) and hexane (50 mL)
  6. washThe ACN layer was washed with hexane (4×50 mL)
  7. concentrationThe ACN layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-55873c359104407cb9746af3526d25da
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687526B2

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