HuagongsheHuagongshe Chemistry Print Report · For research reference only
Butanal → methyl (1RS, 3RS)-cis-1-n-propyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Butanal | HCID 261 | — |
| Reactant | methyl 2-amino-3-(1H-indol-3-yl)propanoate hydrochloride | HCID 2827264 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | methyl (1RS, 3RS)-cis-1-n-propyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate hydrochloride | HCID 86741021 | 38.5% |
Reaction Steps
A mixture of DL-tryptophan methyl ester hydrochloride (33 g), n-butyraldehyde (21.0 g) and methanol (450 ml) is refluxed for 48 hours. After the reaction, the reaction mixture is concentrated to about 1/3 in volume and allowed to stand. The precipitated crystals are collected by filtration and recrystallized from methanol to give methyl (1RS, 3RS)-cis-1-n-propyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate hydrochloride (15.4 g, 38.4%) as colorless prisms, m.p. 205°-207° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04612317 |
| Source dataset | uspto-grants-1986_09 |
| ORD ID | ord-867da906609240f199ae86d2289c2afe |
| Source note | uspto-grants-1986_09 |