Formaldehyde → HCID 13041786, compound

HRID 1903110Notes

Reaction equation

HRID 1903110 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C@H:5]([CH:7]([CH2:17][O:18][CH3:19])[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6])[CH3:2].[CH2:21]=O.O>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[N:6]=[CH:21][C:9]2[NH:10][C:11]3[C:16]([C:8]=2[C:7]=1[CH2:17][O:18][CH3:19])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:20])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 22825899HCID 22825899, compound

Product 1

HCID 13041786HCID 13041786, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

20.3 g of beta-methoxymethyl-tryptophane-ethylester is dissolved in 350 ml of benzene, mixed with 2.48 g of paraformaldehyde and heated for 3.5 h in the water separator. After cooling, the benzene is distilled off, the residue is absorbed in 350 ml of toluene, and after adding 4.5 g of 10% palladium carbon, the mixture is heated with reflux for 20 h. The cooled solution is filtered and concentrated. The residue is chromatographed on silica gel with hexane/ethyl-acetate. The crystallization of the main fraction out of ethylacetate/diisopropylether yields 6.4 g of 4-methoxymethyl-beta-carboline-3-carboxylic-acid-ethylester with a m.p. 118°-119° C.

Workup

  1. temperatureAfter cooling
  2. distillationthe benzene is distilled off
  3. customthe residue is absorbed in 350 ml of toluene
  4. additionafter adding 4.5 g of 10% palladium carbon
  5. temperaturethe mixture is heated
  6. temperaturewith reflux for 20 h
  7. filtrationThe cooled solution is filtered
  8. concentrationconcentrated
  9. customThe residue is chromatographed on silica gel with hexane/ethyl-acetate
  10. customThe crystallization of the main fraction out of ethylacetate/diisopropylether

Sources & evidence

ORD record
ord-e5f3a49d3e344a629e0fa859eb6e656a
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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