Aluminium lithium hydride → Pyrazolo[1,5-a]pyridin-3-ylmethanol

HRID 530808Notes

Reaction equation

HRID 530808 reaction equation
C(=O)(O)N.[N:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14](OC)=[O:15])[CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([CH2:14][OH:15])[CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90419258Methyl pyrazolo[1,5-a]pyridine-3-carboxylate carbamate

Product 1

HCID 14134319Pyrazolo[1,5-a]pyridin-3-ylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl pyrazolo[1,5-a]pyridine-3-carboxylate carbamate (1) (400 mg, 2.10 mmol) in THF (4 mL) was added LiAlH4 (159 mg, 4.20 mmol) at room temperature for 1 h. The reaction mixture was concentrated and 10 mL sat. aq. NaHCO3 was added, extracted with EA (3×10 mL). The organic phase was dried with anhydrous Na2SO4, filtered and concentrated. The residue was purified by Prep-TLC TLC using PE/EtOAc=2/1 to give title compound as oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition10 mL sat. aq. NaHCO3 was added
  3. extractionextracted with EA (3×10 mL)
  4. dry with materialThe organic phase was dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by Prep-TLC TLC

Sources & evidence

ORD record
ord-616d62769ecc4722abec24a2b02f8f51
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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