Water → 2-(3-Hydroxymethyl-pyrazolo[1,5-a]pyridin-2-yl)-propan-2-ol

HRID 549391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 549391
C([O:3][C:4]([C:6]1[C:7]([C:15]([OH:18])([CH3:17])[CH3:16])=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:3][CH2:4][C:6]1[C:7]([C:15]([OH:18])([CH3:16])[CH3:17])=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 578992642-(1-Hydroxy-1-methyl-ethyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester

Produkt 1

HCID 578992362-(3-Hydroxymethyl-pyrazolo[1,5-a]pyridin-2-yl)-propan-2-olAusbeute 117,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-(1-hydroxy-1-methyl-ethyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (1.54 g, 6.20 mmol) in tetrahydrofuran (25 mL) at 0° C. was added lithium aluminum hydride (0.27 g, 6.88 mmol). The mixture was allowed to warm to room temperature and stirred for 16 h. The reaction was cooled in an ice bath and 0.27 mL of water, 0.27 mL of 15% aqueous sodium hydroxide and 0.81 mL of water were sequentially added. The mixture was filtered through a plug of Celite, which was washed with methanol. The filtrate and washes were combined and concentrated in vacuo to give 1.5 g of the title compound as a yellow oil that was used directly in the next step.

Aufarbeitung

  1. temperatureThe reaction was cooled in an ice bath
  2. filtrationThe mixture was filtered through a plug of Celite, which
  3. washwas washed with methanol
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-595c28b43870447ebbb196bad62f60a1
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943652B2

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