Ethyl Acetate → Trans-[2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropyl]methanol
Reaction equation
[CH3:1][C:2]1[CH:18]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[C:13](OCC)=[O:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.O>[CH3:1][C:2]1[CH:18]=[C:5]2[C:6]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][OH:14])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Under nitrogen atmosphere, to a solution of trans-ethyl 2-(2-methylpyrazolo[1,5-a]pyridin-4-yl)cyclopropanecarboxylate (5.40 g, 22.1 mmol) in tetrahydrofuran (150 mL) was added lithium aluminum hydride (0.750 g, 22.1 mmol) at 0° C., and the mixture was stirred for 30 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/hexane) to give the title compound (4.30 g, yield 96%).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with 2 N hydrochloric acid and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by recrystallization (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-acdfb3a474754cc0b0e2196e29fe6049
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08110585B2
Reaction notes
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