Lithium Hydroxide → (1R,2R)-2-(Pyridin-4-yl)cyclopropane-1-carboxylic acid
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[CH2:9][C@H:8]2[C:10]([O:12]CC)=[O:11])=[CH:3][CH:2]=1.[OH-].[Li+]>C1COCC1.O.Cl>[N:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[CH2:9][C@H:8]2[C:10]([OH:12])=[O:11])=[CH:3][CH:2]=1Participants
6
Procedure
To a solution of ethyl trans-2-pyridin-4-ylcyclopropanecarboxylate (0.918 g, 4.80 mmol) in THF (10 mL) and water (10 mL) was added lithium hydroxide (0.345 g, 14.4 mmol). The reaction mixture was allowed to stir at rt for 24 h and then diluted with 2N HCl (10 mL). The mixture was concentrated to give trans-2-pyridin-4-ylcyclopropanecarboxylic acid which was used without purification in the next step. LCMS: (FA) ES+ 164.0, ES-162.1.
Workup
- concentrationThe mixture was concentrated
Sources & evidence
- ORD record
- ord-b055db93d851421b8e9c37884e7a48bb
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795249B2
Reaction notes
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