(2R,5R)-2-(t-butyl)-5-((1R)-3,3-difluorocyclopentyl)-5-phenyl-1,3-dioxolan-4-One → (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acid

HRID 1785257Notes

Reaction equation

HRID 1785257 reaction equation
C([C@H]1[O:9][C:8](=[O:10])[C@@:7]([C@@H:17]2[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6]1)(C)(C)C>CO.[OH-].[Na+].O>[F:22][C:19]1([F:23])[CH2:20][CH2:21][C@@H:17]([C@@:7]([OH:6])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]([OH:10])=[O:9])[CH2:18]1

Participants

5

Reactant 1

HCID 10592061(2R,5R)-2-(t-butyl)-5-((1R)-3,3-difluorocyclopentyl)-5-phenyl-1,3-dioxolan-4-One

Product 1

HCID 10890505(2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acidYield 87.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2.4 g of (2R,5R)-2-(t-butyl)-5-((1R)-3,3-difluorocyclopentyl)-5-phenyl-1,3-dioxolan-4-one in 30 ml of methanol, 10 ml of 1N aqueous sodium hydroxide solution was added, followed by 3 hours' stirring at room temperature. Distilling the methanol off under reduced pressure, the reaction liquid was diluted with water and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted from diethyl ether, and the organic layer was dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, 1.66 g of the title compound was obtained.

Workup

  1. distillationDistilling the methanol off under reduced pressure
  2. customthe reaction liquid
  3. washwashed with diethyl ether
  4. extractionextracted from diethyl ether
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-29385844d9be4267ac23088a4a6e55f9
Source dataset
uspto-grants-2009_03
Patent number
US07504432B2

Reaction notes

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