Methyl iodide → Methyl (1RS, 3RS)-cis-1-butyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioate

HRID 65060Notes

Reaction equation

HRID 65060 reaction equation
[CH2:1]([C@H:5]1[C:17]2[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH2:8][C@@H:7]([CH2:18][OH:19])[NH:6]1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:27](=[S:29])=[S:28].[CH3:30]I>CS(C)=O>[CH2:1]([C@H:5]1[C:17]2[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[CH2:8][C@@H:7]([CH2:18][OH:19])[N:6]1[C:27]([S:29][CH3:30])=[S:28])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 70455657HCID 70455657, compound

Product 1

HCID 86741007Methyl (1RS, 3RS)-cis-1-butyl-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as described in Example 13 by using (1RS, 3RS)-cis-1-butyl-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline (1.05 g), triethylamine (0.53 g), CS2 (0.50 g), methyl iodide (0.95 g) and dimethylsulfoxide (8 ml), there is prepared the title compound (0.85 g, 61%) as white powder. NMR (CDCl3, δ): 0.96 (t, J=7.0 Hz, 3H, C1 --(CH2)3CH3), 2.72 (s, 3H, CSSCH3), Mass m/e: 348 (M+), 300 (M+ --CH3SH).

Sources & evidence

ORD record
ord-6449a7b1fb88464e80f9243db486f44b
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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