Aluminium lithium hydride → (1-Cyclopropyl-1H-indazol-5-yl) methanol

HRID 73107Notes

Reaction equation

HRID 73107 reaction equation
[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][C:9]([C:13](OC)=[O:14])=[CH:10][CH:11]=3)[CH:6]=[N:5]2)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]1([N:4]2[C:12]3[C:7](=[CH:8][C:9]([CH2:13][OH:14])=[CH:10][CH:11]=3)[CH:6]=[N:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66837925Methyl 1-cyclopropyl-1H-indazole-5-carboxylate

Product 1

HCID 66837867(1-Cyclopropyl-1H-indazol-5-yl) methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 1-cyclopropyl-1H-indazole-5-carboxylate (400 mg, 1.8 mmol, step-1 of Example 28) in THF (15 mL) was added LiAlH4 (70 mg, 1.8 mmol) at 0° C. The reaction mixture was stirred for 1 hr at room temperature, and quenched with saturated aqueous NH4Cl (20 mL). The mixture was diluted with DCM (80 mL), dried over Na2SO4, filtered through a pad of Celite (registered trademark) the filtrate was concentrated to give 386 mg (quant.) of the titled compound as pale yellow oil.

Workup

  1. customquenched with saturated aqueous NH4Cl (20 mL)
  2. additionThe mixture was diluted with DCM (80 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered through a pad of Celite (registered trademark) the filtrate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-ffe41fb35518440f99abb7e853bdc907
Source dataset
uspto-grants-2014_09
Patent number
US08829026B2

Reaction notes

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