Hydrochloric Acid → (1S,2R)-2-(4-Pyridinylmethyl)cyclohexanecarboxylic acid

HRID 2188337Notes

Reaction equation

HRID 2188337 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([C:8]([C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[C:16]([OH:18])=[O:17])=O)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[Zn].Cl[Hg]Cl>[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[C:16]([OH:18])=[O:17])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69827195HCID 69827195, compound

Product 1

HCID 57247235(1S,2R)-2-(4-Pyridinylmethyl)cyclohexanecarboxylic acid

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24085Mercuric ChlorideCatalystHCID 311Citric AcidSolvent

Procedure

A mixture of 8.5 M hydrochloric acid (10.5 mL), Zn (5.57 g, 85.2 mmol), and HgCl2 (0.557 g, 2.1 mmol) was stirred for 15 min, and then (1S, 2R)-2-(4-pyridylcarbonyl)cyclohexanecarboxylic acid (0.30 g, 1.3 mmol) was added. The reaction mixture was stirred at reflux for 20 h, and then diluted with 10% citric acid (75 mL), and then adjusted to pH=4 by addition of 10 M NaOH. The reaction mixture was extracted with ethyl acetate, washed with sat. brine, dried over MgSO4, filtered, and evaporated to give (1S, 2R)-2-(4-pyridylmethyl)-cyclohexanecarboxylic acid, as a white semi-solid (0.25 g, 90%).

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureat reflux for 20 h
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washwashed with sat. brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-37f21c6a960146079d8d3fcb13e3e091
Source dataset
uspto-grants-2002_06
Patent number
US06410781B1

Reaction notes

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