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

HRID 65074

Reaction equation

HRID 65074 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]([CH3:16])[NH:4]1.C(N(CC)CC)C.[C:24](=[S:26])=[S:25].[CH3:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=1>CO.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]([CH3:16])[N:4]1[C:24]([S:26][CH2:27][C:28]1[CH:35]=[CH:34][C:31]([CH3:32])=[CH:30][CH:29]=1)=[S:25]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 77224-Methylbenzyl chlorideHCID 8471TriethylamineHCID 13375562(1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 133929914-Methylbenzyl (1S, 3S)-3-hydroxymethyl-1-methyl-1,2,3,4-tetrahydro-beta-carboline-2-carbodithioateYield 80%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

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), 4-methylbenzyl chloride (1.4 g) and dimethylsulfoxide (10 ml), there is prepared the title compound (1.58 g, 80%) as white powder, [α]D20 +63.2° (c=0.5, methanol); NMR (CDCl3, δ): 2.31 (s, 3H, ##STR18## 4.66 (s, 2H, ##STR19## Mass m/e: 396 (M+), 258 (M+ -- ##STR20##

Sources & evidence

ORD record
ord-495d03aaaf604437bcda0dbef8bf1b69
Source dataset
uspto-grants-1986_09
Patent number
US04612317

Linked notes

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