Lithium hydroxide, monohydrate → (1R,2R)-2-(4-Fluoro-phenyl)-cyclopropanecarboxylic acid

HRID 1069028Notes

Reaction equation

HRID 1069028 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[C:11](N2C3CC4C(C)(C)C3(CC4)CS2(=O)=O)=[O:12])=[CH:4][CH:3]=1.[OH2:27].[OH-].[Li+]>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([OH:12])=[O:27])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 85216779HCID 85216779, compound

Product 1

HCID 10535366(1R,2R)-2-(4-Fluoro-phenyl)-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of the product from step g) (3.74 g) and lithium hydroxide monohydrate (4.11 g) in tetrahydrofuran (100 ml) and water (3 ml) was stirred at 50° C. for 24 hours. The reaction mixture was concentrated in vacuo, and the residue dissolved in water (100 ml), acidified with 2N HCl and extracted into dichloromethane (3×75 ml). The organics were dried and concentrated. Purification (SiO2, isohexane:diethylether 2:1 as eluant) gave the subtitle compound as a colourless solid (1.78 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in water (100 ml)
  3. extractionextracted into dichloromethane (3×75 ml)
  4. customThe organics were dried
  5. concentrationconcentrated
  6. customPurification (SiO2, isohexane:diethylether 2:1 as eluant)

Sources & evidence

ORD record
ord-34d31262dd284301a235600254d6aea5
Source dataset
uspto-grants-2001_06
Patent number
US06251910B1

Reaction notes

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