Indole → HCID 19892079, compound

HRID 893330Notes

Reaction equation

HRID 893330 reaction equation
[Na].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.O=[C:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20]C)=[O:19])[CH2:14][CH2:13]1>CO>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH:13]=1

Participants

5

Reactant 3

HCID 798IndoleHCID 226643Methyl 4-oxocyclohexanecarboxylateHCID 5360545Sodium

Product 1

HCID 19892079HCID 19892079, compoundYield 28.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 50 mL of methanol is added sodium (3.32 g, 144.3 mmol). After the metal has dissolved indole (2.89 g, 24.6 mmol) and methyl 4-oxocyclohexanecarboxylate (5.0 g, 32.0 mmol) are added. The mixture is heated to reflux for 3 hours. The methanol is removed under reduced pressure and the residue partitioned between water and methylene chloride. The organic layer is discarded. The aqueous layer is acidified to pH 5 and extracted with three portions of methylene chloride. The combined organics are dried over sodium sulfate and evaporated to give 4-indolyl-3-cyclohexenecarboxylic acid (1.71 g). The material is hydrogenated in methanol (75 mL) under 50 psi of hydrogen int he presence of 5% palladium on carbon (0.5 g). After filtration and removal of solvent, the product is obtained as a mixture of diastereomers.

Workup

  1. additionare added
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 3 hours
  4. customThe methanol is removed under reduced pressure
  5. customthe residue partitioned between water and methylene chloride
  6. extractionextracted with three portions of methylene chloride
  7. dry with materialThe combined organics are dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-09269720fd474d378005d8da444bf080
Source dataset
uspto-grants-1992_06
Patent number
US05124332

Reaction notes

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