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

HRID 65064Notes

Reaction equation

HRID 65064 reaction equation
[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]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:4]1.C(N(CC)CC)C.[C:29](=[S:31])=[S:30].[CH3:32]I>CS(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]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:4]1[C:29]([S:31][CH3:32])=[S:30]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 86741014(1RS, 3RS)-cis-3-hydroxymethyl-1-phenyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 86741013Methyl (1RS, 3RS)-cis-3-hydroxymethyl-1-phenyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateYield 78.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as described in Example 13 by using (1RS, 3RS)-cis-3-hydroxymethyl-1-phenyl-1,2,3,4-tetrahydro-β-carboline (300 mg) [J.A.C.S., 102, 6976 (1980)], triethylamine (220 mg), CS2 (160 mg), methyl iodide (306 mg) and dimethylsulfoxide (6 ml), there is prepared the title compound (310 mg, 78%) as white powder.

Sources & evidence

ORD record
ord-f8c6ec9088e142c8b9185f979e4f3ff4
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Reaction notes

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