Lithium Hydroxide → HCID 83669226, Verbindung

HRID 575847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 575847
[Li+].[OH-].[C:3]1([C:12]([O:14]CC)=[O:13])[C:8]2[CH2:9][CH2:10][CH2:11][C:7]=2[CH:6]=[CH:5][N:4]=1>O.CO>[C:3]1([C:12]([OH:14])=[O:13])[C:8]2[CH2:9][CH2:10][CH2:11][C:7]=2[CH:6]=[CH:5][N:4]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 450986655H-Cyclopenta[c]pyridine-1-carboxylicacid,6,7-dihydro-,ethylester(9CI)

Produkt 1

HCID 83669226HCID 83669226, VerbindungAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A 2N solution of LiOH (50 mL) in water was slowly added to the title compound of step 1 (10 g, 52.4 mmol) in MeOH (250 mL) at 0° C. The mixture was allowed to warm to rt and stirred for 30 min. The MeOH was reduced under vacuum and the residual aqueous solution was washed with EtOAc. The organic phase was re-extracted with water. The combined aqueous extracts were acidified to pH=2 with 1N HCl. The water was removed and preparative HPLC gave the title compound (5.4 g, 63%) as a white solid. 1H NMR (CD3OD, 400 MHz): δ 8.45 (d, J=5.6 Hz, 1H), 7.88 (d, J=5.6 Hz, 1H), 3.39 (t, J=8.0, 7.6 Hz, 2H), 3.16 (d, t, J=8.0, 7.6 Hz, 2H), 2.16-2.20 (m, 2H).

Aufarbeitung

  1. washthe residual aqueous solution was washed with EtOAc
  2. extractionThe organic phase was re-extracted with water
  3. customThe water was removed

Quellen und Nachweise

ORD-Eintrag
ord-d393120bd6b94271b926266c323e8af5
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034900B2

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