Lithium Hydroxide → 2-oxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-7-carboxylic acid

HRID 887133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887133
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].ClC1[N:14]=[C:13]2[CH:15]([C:18]([O:20]C)=[O:19])[CH2:16][CH2:17]C2=CC=1>CO>[O:1]=[C:5]1[NH:14][C:13]2[CH:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17][C:2]=2[CH:3]=[CH:4]1

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57907634HCID 57907634, Verbindung

Produkt 1

HCID 242717622-oxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-7-carboxylic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a 15 mL mixture of tetrahydrofuran, methanol, and a 1.0 N aqueous LiOH solution in a 3:1:1 ratio was added 0.242 g (1.14 mmol) of methyl 2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate from Step C above. The resulting mixture was stirred at ambient temperature for 1 h. The solution was evaporated in vacuo and the resulting light brown residue was purified by reverse phase HPLC (YMC Pack Pro C18, 100×20 mm I.D. column, 0-60% 0.01% trifluoroacetic acid in acetonitrile/0.01% trifluoroacetic acid in water gradient) to give the title compound as a brown oil (184 mg, 90%). LC-MS: m/z (E/S) 180.0 (MH)+.

Aufarbeitung

  1. customThe solution was evaporated in vacuo
  2. customthe resulting light brown residue was purified by reverse phase HPLC (YMC Pack Pro C18, 100×20 mm I.D. column, 0-60% 0.01% trifluoroacetic acid in acetonitrile/0.01% trifluoroacetic acid in water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-f972c714e42f405bb7d09f82687944c1
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247415B2

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