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Pentanal → methyl (1RS, 3RS)-cis-1-butyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate hydrochloride
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Pentanal | HCID 8063 | — |
| 反応物 | methyl 2-amino-3-(1H-indol-3-yl)propanoate hydrochloride | HCID 2827264 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 生成物 | methyl (1RS, 3RS)-cis-1-butyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate hydrochloride | HCID 86741020 | 53% |
反応手順
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.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US04612317 |
| 出典データセット | uspto-grants-1986_09 |
| ORD ID | ord-ff85d55b0bb44c4a897f042a092c8404 |
| 出典メモ | uspto-grants-1986_09 |