HCID 54197900, compound → HCID 69827195, compound

HRID 1265323Notes

Reaction equation

HRID 1265323 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[C:15]([OH:17])=[O:16])=[O:8])=[CH:3][CH:2]=1>[OH-].[Na+]>[N:1]1[CH:6]=[CH:5][C:4]([C:7]([C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[C:15]([OH:17])=[O:16])=[O:8])=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 54197900HCID 54197900, compound

Product 1

HCID 69827195HCID 69827195, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

Cis-2-(4-pyridylcarbonyl)cyclohexanecarboxylic acid was dissolved in 10% sodium hydroxide (300 mL) and stirred at 20° C. for 16 h. The aqueous solution was extracted with diethyl ether (200 mL) and then acidified to pH=4 by addition of 6 M hydrochloric acid. The resulting precipitate was collected and recrystallized from hot water, to give (1S,2R)-2-(4-pyridylcarbonyl)-cyclohexanecarboxylic acid, as a white solid (4.8 g, 40% from cis-1,2-cyclohexanedicarboxylic anhydride).

Workup

  1. extractionThe aqueous solution was extracted with diethyl ether (200 mL)
  2. additionacidified to pH=4 by addition of 6 M hydrochloric acid
  3. customThe resulting precipitate was collected
  4. customrecrystallized from hot water

Sources & evidence

ORD record
ord-b0f4ce491e6349b48a43aaf4d226f555
Source dataset
uspto-grants-2003_04
Patent number
US06545160B2

Reaction notes

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