Methanol → (4H,5H,6H,7H-pyrazolo(1,5-a)pyridin-2-yl)methanol

HRID 1158862Notes

Reaction equation

HRID 1158862 reaction equation
CO.[Li+].[BH4-].C([O:7][C:8]([C:10]1[CH:18]=[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][N:12]2[N:11]=1)=O)C>C1COCC1>[N:11]1[N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]2=[CH:18][C:10]=1[CH2:8][OH:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 11845784Ethyl 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylate

Product 1

HCID 11845786(4H,5H,6H,7H-pyrazolo(1,5-a)pyridin-2-yl)methanolYield 102.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

MeOH (0.29 mL) was added to the THF (19 mL) solution of LiBH4 (cont. 90%) (174 mg) under a nitrogen atmosphere at room temperature, then 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-2-carboxylic acid ethyl ester (862 mg) was added to the suspension and stirred for 1 h at room temperature and 1.5 h at 40° C. The mixture was quenched with 1 mol/L HCl at pH 1 and stirred for 1 h at room temperature. Solid K2CO3 was added to the solution to adjust pH to 8 and the mixture was extracted with AcOEt. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to afford titled compound as pale yellow oil (691 mg, 95%).

Workup

  1. customThe mixture was quenched with 1 mol/L HCl at pH 1
  2. stirringstirred for 1 h at room temperature
  3. additionSolid K2CO3 was added to the solution
  4. extractionthe mixture was extracted with AcOEt
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e52a0e0033e84298b2f0c2643e1c4da8
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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