Formaldehyde → H-Tpi-ome hcl

HRID 1732136Notes

Reaction equation

HRID 1732136 reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6].[CH2:18]=O>CO>[ClH:1].[CH2:18]1[C:9]2[NH:10][C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]=2[CH2:7][C@@H:5]([C:4]([O:3][CH3:2])=[O:17])[NH:6]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 12655248H-Tpi-ome hclYield 82.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.09 g of L-tryptophan methyl ester hydrochloride are dissolved in 60 ml of methanol. 1.89 g of 35% formalin are added thereto, and the mixture is stirred at room temperature overnight. After distilling off the solvent, the resulting residue is recrystallized from methanol. 4.42 g of methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate hydrochloride are obtained as colorless needles. Yield: 82.9%

Workup

  1. distillationAfter distilling off the solvent
  2. customthe resulting residue is recrystallized from methanol

Sources & evidence

ORD record
ord-0e0dad3fee384a8eaa0b1c0eb8890aaf
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

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