Sodium Hydroxide → 4-benzyl-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic Acid

HRID 1253292Notes

Reaction equation

HRID 1253292 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5]1([CH2:25][CH3:26])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][CH:13]=3.[OH-].[Na+]>C(O)C>[CH2:18]([CH:8]1[C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[C:5]([CH2:25][CH3:26])([CH2:4][C:3]([OH:27])=[O:2])[O:6][CH2:7]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13911142HCID 13911142, compound

Product 1

HCID 606184-benzyl-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic AcidYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-benzyl-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester (0.67 g, 1.8 mmol) in 30 mL of ethanol was added 30 mL of 10% solution of sodium hydroxide and heated at reflux for 2 hours under nitrogen. The reaction mixture was then cooled and concentrated in vacuo, diluted with 20 mL of H2O and extracted with ether. The aqueous layer was then acidified with 2N HCl and extracted with chloroform (3×100 mL), dried over magnesium sulfate and concentrated in vacuo to give 0.516 g (80%) of the product, m.p. 142°-143° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours under nitrogen
  3. temperatureThe reaction mixture was then cooled
  4. concentrationconcentrated in vacuo
  5. additiondiluted with 20 mL of H2O
  6. extractionextracted with ether
  7. extractionextracted with chloroform (3×100 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5bd05d60c1eb494b8db64deedec24238
Source dataset
uspto-grants-1988_05
Patent number
US04748252

Reaction notes

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