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

HRID 1802764Notes

Reaction equation

HRID 1802764 reaction equation
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

Participants

6

Reactant 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

Product 1

HCID 578992362-(3-Hydroxymethyl-pyrazolo[1,5-a]pyridin-2-yl)-propan-2-olYield 117.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-246cc492a48f4ad983da00b9b02abcf2
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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