HCID 68715913, Verbindung → 3,3-Difluorocyclopentane-1-carboxylic acid

HRID 920808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920808
[F:1][C:2]1([F:17])[CH2:6][CH2:5][CH:4]([C:7]([O:9]CC2C=CC=CC=2)=[O:8])[CH2:3]1>CCOC(C)=O.[Pd]>[F:1][C:2]1([F:17])[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1

Komponenten

4

Edukt 1

HCID 68715913HCID 68715913, Verbindung

Produkt 1

HCID 534038373,3-Difluorocyclopentane-1-carboxylic acidAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of Intermediate 332B (0.07 g, 0.291 mmol) in EtOAc (2 mL) was added 10% Pd/C (0.016 g, 0.015 mmol) and the resulting mixture was stirred for 16 h under an atmosphere of hydrogen (15 psi, balloon pressure). The reaction mixture was filtered through a pad of CELITE® and the filter cake was washed with EtOAc. The combined filtrate was concentrated under reduced pressure to afford Intermediate 332C as a colorless oil (0.035 g, 76% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.41 (br. s., 1H), 3.04-2.94 (m, 1H), 2.39-2.23 (m, 2H), 2.20-2.01 (m, 3H), 1.95-1.84 (m, 1H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of CELITE®
  2. washthe filter cake was washed with EtOAc
  3. concentrationThe combined filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e8acacd8f6bb49fab0973a4f6f1a15e0
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273058B2

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