Carbon Disulfide → 4-Chlorobenzyl (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65057

Reaktionsgleichung

Reaktionsgleichung von HRID 65057
[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.[OH-].[Na+].[C:19](=[S:21])=[S:20].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][CH:24]=1>CO.C(O)C>[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:19]([S:21][CH2:27][C:26]1[CH:29]=[CH:30][C:23]([Cl:22])=[CH:24][CH:25]=1)=[S:20]

Komponenten

7

Edukt 4

HCID 6348Carbon DisulfideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 13375562(1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline

Produkt 1

HCID 133755404-Chlorobenzyl (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

In the same manner as described in Example 13 by using (1S,3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-β-carboline (216 mg), 2N NaOH (1.5 ml), CS2 (228 mg), 4-chlorobenzyl chloride (480 mg) and 80% ethanol (5 ml), there is prepared the title compound (292 mg, 70%) as white powder, [α]D20 +136.4° (c=1.1, methanol). NMR (CDCl3, δ): 1.63 (d, J=6.5 Hz, 3H, C1 --CH3), 4.57 (s, 2H, CSSCH2 -C6H4 -p-Cl), Mass m/e: 291 (M+ -CH2C6H4 -p-Cl), 258 (M+ -p-Cl-C6H4 -CH2SH).

Quellen und Nachweise

ORD-Eintrag
ord-7be0c4bac6054791851d90f3dcb5e6e9
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612317

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