Pentanal → methyl (1RS, 3RS)-cis-1-butyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate hydrochloride

HRID 65080

Reaction equation

HRID 65080 reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:17])[CH: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].[CH3:18][CH2:19][CH2:20][CH2:21][CH:22]=O>CO>[ClH:1].[CH2:19]([C@H: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)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 8063PentanalHCID 2827264methyl 2-amino-3-(1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 86741020methyl (1RS, 3RS)-cis-1-butyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate hydrochlorideYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of DL-tryptophan methyl ester hydrochloride (30.49 g), n-valeraldehyde (12.4 g) and methanol (400 ml) is refluxed for 48 hours and then concentrated to about 1/5 volume. After cooling, the precipitates are separated by filtration and recrystallized from methanol to give methyl (1RS, 3RS)-cis-1-butyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate hydrochloride (20.5 g, 53%), m.p. 218° C. (decomp.) The hydrochloride thus obtained is treated with aqueous ammonia and recrystallized from diisopropyl ether-isopropanol to give the corresponding free base, m.p. 85°-87° C.

Workup

  1. temperatureis refluxed for 48 hours
  2. concentrationconcentrated to about 1/5 volume
  3. temperatureAfter cooling
  4. customthe precipitates are separated by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ff85d55b0bb44c4a897f042a092c8404
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Linked notes

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