Sodium Hydroxide → Ethyl octahydro-1H-indole-2-carboxylate

HRID 1388291Notes

Reaction equation

HRID 1388291 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[OH-].[Na+]>FC(F)(F)C(O)=O.CCOCC.O=[Pt]=O>[NH:1]1[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][CH:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 13069248Ethyl octahydro-1H-indole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Dissolve 27.0 g of ethyl indole-2-carboxylate in 250 ml of trifluoroacetic acid. Add 2.05 g of platinium oxide, hydrogenate the mixture at 50 lb/in2 at room temperature. Filter the mixture and concentrate the filtrate in vacuo to give a residue. Suspend the residue in ether and treat with cold dilute sodium hydroxide solution. Dry the organic layer over magnesium sulfate and concentrate it to give ethyl octahydroindole-2-carboxylate, a pale yellow oil.

Workup

  1. filtrationFilter the mixture
  2. concentrationconcentrate the filtrate in vacuo
  3. customto give a residue
  4. dry with materialDry the organic layer over magnesium sulfate
  5. concentrationconcentrate it

Sources & evidence

ORD record
ord-890918c2f3924c76bf937841fa51faae
Source dataset
uspto-grants-1984_02
Patent number
US04431644

Reaction notes

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