Carbon Disulfide → HCID 13392989, Verbindung

HRID 65073

Reaktionsgleichung

Reaktionsgleichung von HRID 65073
[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]([CH3:16])[NH:4]1.C(N(CC)CC)C.[C:24](=[S:26])=[S:25].[CH2:27](I)[CH2:28][CH2:29][CH3:30]>CN(C)C=O>[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[C@H:5]([CH3:16])[N:4]1[C:24]([S:26][CH2:27][CH2:28][CH2:29][CH3:30])=[S:25]

Komponenten

6

Edukt 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10962Butyl iodideHCID 13375562(1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline

Produkt 1

HCID 13392989HCID 13392989, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In the same manner as described in Example 34 by using (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-β-carboline (1.08 g), triethylamine (1.01 g), CS2 (0.76 g), n-butyl iodide (1.84 g) and dimethylformamide (8 ml), there is prepared the title compound (1.3 g, 75%) as colorless needles, m.p. 110°-113° C. (recrystallized from aqueous ethanol, [α]D20 +181.8° (c=1.0, methanol); NMR (CDCl3, δ): 0.97 (m, 3H, --(CH2)3CH3); Mass m/e: 348 (M+), 258 (M+ --C4H9SH).

Quellen und Nachweise

ORD-Eintrag
ord-713b7b57c8b448f0b42a61bec1909fb3
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612317

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