Triethylamine → (1-pyrrolidin-1-ylindan-5-yl)propynoic Acid

HRID 735030

Reaktionsgleichung

Reaktionsgleichung von HRID 735030
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:6][CH2:5]2.[C:16]([OH:20])(=[O:19])[C:17]#[CH:18].C(N(CC)CC)C>C(#N)C.[Cu]I>[N:11]1([CH:7]2[C:8]3[C:4](=[CH:3][C:2]([C:18]#[C:17][C:16]([OH:20])=[O:19])=[CH:10][CH:9]=3)[CH2:5][CH2:6]2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 10110Propiolic AcidHCID 688183461-(5-Iodoindan-1-yl)pyrrolidine

Produkt 1

HCID 68817830(1-pyrrolidin-1-ylindan-5-yl)propynoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Under an argon atmosphere at 0° C., 0.5 g (1.59 mmol) of 1-(5-iodoindan-1-yl)pyrrolidine and 123 mL (2 mmol) of propynoic acid are dissolved in 25 mL of acetonitrile. 0.66 mL (4.79 mmol) of triethylamine, 30 mg (0.16 mmol) of copper (I) iodide, and 80 mg (0.11 mmol) of ditriphenylphosphine palladium dichloride are added to this solution and the mixture is stirred for 2 hours, while the solution is allowed to come up to ambient temperature. The purification is carried out by preparative HPLC (eluant: dichloromethane/methanol/ammonia (8:2:0.2)). Yield 0.1 g (24.5% of theory); C16H17NO2 (M=255.31); calc.: molecular ion peak (M+H)+: 256; found: molecular ion peak (M+H)+: 256.

Aufarbeitung

  1. customto come up to ambient temperature
  2. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-ea9c97f40edd4f55833fa381371bd748
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592373B2

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