Ethyl Acetate → Trans-[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanol

HRID 1639751Notes

Reaction equation

HRID 1639751 reaction equation
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[C:14](OCC)=[O:15])=[N:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.O>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][CH:7]=[C:8]2[C@@H:11]2[CH2:13][C@H:12]2[CH2:14][OH:15])=[N:3]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131729433trans-Ethyl 2-(2-methyl-2h-indazol-4-yl)cyclopropanecarboxylate

Product 1

HCID 66720579Trans-[2-(2-methyl-2H-indazol-4-yl)cyclopropyl]methanolYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, to a solution of trans-ethyl 2-(2-methyl-2H-indazol-4-yl)cyclopropanecarboxylate (3.89 g, 15.9 mmol) in tetrahydrofuran (100 mL) was added lithium aluminum hydride (0.540 g, 15.9 mmol) at 0° C., and the mixture was stirred for 10 min. To the reaction mixture were added ethyl acetate, water and 10% aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed with 2 N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by recrystallization (ethyl acetate) to give the title compound (3.00 g, yield 93%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 2 N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by recrystallization (ethyl acetate)

Sources & evidence

ORD record
ord-2ae571055741400c99d213106706a4b4
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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