Water → trans-2-(3-Fluoro-phenyl)-cyclopropanecarboxylic acid
Reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)=[O:5])C.[OH-].[K+].O>CO>[F:15][C:11]1[CH:10]=[C:9]([C@@H:7]2[CH2:8][C@H:6]2[C:4]([OH:5])=[O:3])[CH:14]=[CH:13][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of rac-trans 2-(3-fluoro-phenyl)-cyclopropanecarboxylic acid ethyl ester (13.0 g, 0.062 mol) in MeOH (310 mL) was added a solution of KOH (35.0 g, 0.625 mol) in MeOH (150 mL) at 0° C. After addition of the base the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured into water and extracted with methylene chloride (2×50 mL). The aqueous layer was acidified with 10% HCl. The resulting mixture was extracted with methylene chloride (2×150 mL). The combined organic layers were dried over Na2SO4 and evaporated to dryness to give rac-trans-2-(3-fluoro-phenyl)-cyclopropanecarboxylic acid as colorless crystals (9.5 g, 85%). Separation of the isomers by chiral SFC (Method D) gave the title compound (1S,2S)-2-(3-fluoro-phenyl)cyclopropanecarboxylic acid IM47 as colorless crystals (3.27 g, 17% overall yield from 3-fluorostyrene) sufficiently pure for the next step. Specific optical rotation +263.4° [α]D20 (C=1% MeOH)
Workup
- additionAfter addition of the base the reaction mixture
- extractionextracted with methylene chloride (2×50 mL)
- extractionThe resulting mixture was extracted with methylene chloride (2×150 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-71f80a9c2b7f4941a62cceef67202d5b
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598213B2
Reaction notes
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