Sodium Hydroxide → (1S,3S)-1-Ethyl-2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indole-3-carboxylic acid

HRID 1249088Notes

Reaction equation

HRID 1249088 reaction equation
[CH2:1]([C@H:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][C@@H:5]([C:16]([O:18]C)=[O:17])[NH:4]1)[CH3:2].[OH-].[Na+]>CO>[CH2:1]([C@H:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH2:6][C@@H:5]([C:16]([OH:18])=[O:17])[NH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12789174HCID 12789174, compound

Product 1

HCID 178220(1S,3S)-1-Ethyl-2,3,4,9-tetrahydro-1H-pyrido(3,4-b)indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (1RS,3RS)-cis-1-ethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (5.0 g) is dissolved in methanol (30 ml) and thereto is added 1N NaOH (30 ml). The mixture is stirred at room temperature for 1.5 hour, and the solvent is distilled off. The residue is dissolved in water and is acidified with 5% HCl. The precipitated crystals are collected by filtration, washed with water and dried to give the title compound (3.40 g, 72%) as colorless needles, m.p. 236°-237° C. (recrystallized from aqueous ethanol).

Workup

  1. distillationthe solvent is distilled off
  2. dissolutionThe residue is dissolved in water
  3. filtrationThe precipitated crystals are collected by filtration
  4. washwashed with water
  5. customdried
  6. customto give
  7. customthe title compound (3.40 g, 72%) as colorless needles, m.p. 236°-237° C. (recrystallized from aqueous ethanol)

Sources & evidence

ORD record
ord-2c22a98e4ff64a9eb01ba508026d1937
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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