3-(3-Cyano-phenyl)-2-pyrrolidin-2-ylidene-propionic acid methyl ester → 3-[2-(4,5-Dihydro-3H-pyrrol-2-yl)-ethyl]benzonitrile

HRID 901334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901334
COC(=O)[C:4](=[C:14]1[CH2:18][CH2:17][CH2:16][NH:15]1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=1>C(Cl)Cl>[N:15]1[CH2:16][CH2:17][CH2:18][C:14]=1[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[C:12]#[N:13]

Komponenten

3

Edukt 1

HCID 692550583-(3-Cyano-phenyl)-2-pyrrolidin-2-ylidene-propionic acid methyl ester

Produkt 1

HCID 692552573-[2-(4,5-Dihydro-3H-pyrrol-2-yl)-ethyl]benzonitrileAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A flask containing 3-(3-Cyano-phenyl)-2-pyrrolidin-2-ylidene-propionic acid methyl ester (0.25 g, 0.977 mmol), and H3BO3 (0.0664 g, 1.07 mmol) is heated to 180° C. for 2 h. The reaction is cooled to RT and treated with H20 (0.8 mL) and CH2Cl2 (2 mL) and the resulting mixture is vigorously stirred. The organic phase is separated, diluted with CH2Cl2 (15 mL) dried over Na2SO4 and concentrated. Purification by flash chromatography (2:1:1/EtOAc:CH2Cl2:hexanes) yields the title compound (0.07 g, 0.35 mmol). 1H NMR (CDCl3, 300 MHz) 7.63-7.35(m, 4H), 4.08-3.95(m, 2H), 3.18-3.01(m, 4H), 2.87-2.73(m, 2H), 2.20-2.06(m, 2H).

Aufarbeitung

  1. temperatureThe reaction is cooled to RT
  2. customThe organic phase is separated
  3. additiondiluted with CH2Cl2 (15 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by flash chromatography (2:1:1/EtOAc:CH2Cl2:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6f15372f2b284e84b213ef2143059c7f
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361663B2

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